Treatment of duchenne muscular dystrophy

ABSTRACT

There are disclosed compound of Formula (1): A 1 , A 2 , A 3  and A 4  which may be the same or different, represent N or CR 1 , X is a divalent group selected from O, S(O) n , C═W, NR 4 , NC(═O)R 5  and CR 6 R 7 , W is O, S, NR 20 , Y is N or CR 8 , one of R 4 , R 5 , R 6 , R 8 , R 9  and NR 20  represents -L-R 3 , in which L is a single bond or a linker group, additionally, R 1 , R 3 -R 9 , which may be the same or different, independently represent hydrogen or a substituent and R 20  represents hydrogen, hydroxyl, alkyl optionally substituted by aryl, alkoxy optionally substituted by aryl, aryl, CN, optionally substituted alkoxy, optionally substituted aryloxy, optionally substitute alkanoyl, optionally substituted aroyl, NO 2 , NR 30 R 31 , in which R 30  and R 31 , which may be the same or different, represent hydrogen, optionally substituted alkyl or optionally substituted aryl; additionally, one of R 30  and R 31  may represent optionally substituted alkanoyl or optionally substituted aroyl, n represents an integer from 0 to 2, in addition, when an adjacent pair of A 1 -A 4  each represent CR 1 , then the adjacent carbon atoms, together with their substituents may form a ring B, when X is CR 6 R 7 , R 6  and R 7 , together with the carbon atom to which they are attached may form a ring C, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the therapeutic and/or prophylactic treatment of Duchenne muscular dystrophy, Becker muscular dystrophy or cachexia.

The present invention relates to a method of treatment of Duchennemuscular dystrophy.

Duchenne muscular dystrophy (DMD) is a common, genetic neuromusculardisease associated with the progressive deterioration of musclefunction, first described over 150 years ago by the French neurologist,Duchenne de Boulogne, after whom the disease is named. DMD has beencharacterized as an X-linked recessive disorder that affects 1 in 3,500males caused by mutations in the dystrophin gene. The gene is thelargest in the human genome, encompassing 2.6 million base pairs of DNAand containing 79 exons. Approximately 60% of dystrophin mutations arelarge insertion or deletions that lead to frameshift errors downstream,whereas approximately 40% are point mutations or small frameshiftrearrangements. The vast majority of DMD patients lack the dystrophinprotein. Becker muscular dystrophy is a much milder form of DMD causedby reduction in the amount, or alteration in the size, of the dystrophinprotein. The high incidence of DMD (1 in 10,000 sperm or eggs) meansthat genetic screening will never eliminate the disease, so an effectivetherapy is highly desirable.

A number of natural and engineered animal models of DMD exist, andprovide a mainstay for preclinical studies (Allamand, V. & Campbell, K.P. Animal models for muscular dystrophy: valuable tools for thedevelopment of therapies. Hum. Mol. Genet. 9, 2459-2467 (2000).)Although the mouse, cat and dog models all have mutations in the DMDgene and exhibit a biochemical dystrophinopathy similar to that seen inhumans, they show surprising and considerable variation in terms oftheir phenotype. Like humans, the canine (Golden retriever musculardystrophy and German short-haired pointer) models have a severephenotype; these dogs typically die of cardiac failure. Dogs offer thebest phenocopy for human disease, and are considered a high benchmarkfor preclinical studies. Unfortunately, breeding these animals isexpensive and difficult, and the clinical time course can be variableamong litters.

The mdx mouse is the most widely used model due to availability, shortgestation time, time to mature and relatively low cost (Bulfield, G.,Siller, W. G., Wight, P. A. & Moore, K. J. X chromosome-linked musculardystrophy (mdx) in the mouse. Proc. Natl. Acad. Sci. USA 81, 1189-1192(1984)).

Since the discovery of the DMD gene about 20 years ago, varying degreesof success in the treatment of DMD have been achieved in preclinicalanimal studies, some of which are being followed up in humans. Presenttherapeutic strategies can be broadly divided into three groups: first,gene therapy approaches; second, cell therapy; and last, pharmacologicaltherapy. Gene- and cell-based therapies offer the fundamental advantageof obviating the need to separately correct secondary defects/pathology(for example, contractures), especially if initiated early in the courseof the disease. Unfortunately, these approaches face a number oftechnical hurdles. Immunological responses against viral vectors,myoblasts and newly synthesized dystrophin have been reported, inaddition to toxicity, lack of stable expression and difficulty indelivery.

Pharmacological approaches for the treatment of muscular dystrophydiffer from gene- and cell-based approaches in not being designed todeliver either the missing gene and/or protein. In general, thepharmacological strategies use drugs/molecules in an attempt to improvethe phenotype by means such as decreasing inflammation, improvingcalcium homeostasis and increasing muscle progenitor proliferation orcommitment. These strategies offer the advantage that they are easy todeliver systemically and can circumvent many of the immunological and/ortoxicity issues that are related to vectors and cell-based therapies.Although investigations with corticosteroids and sodium cromoglycate, toreduce inflammation, dantrolene to maintain calcium homeostasis andclenbuterol to increase muscle strength, have produced promising resultsnone of these potential therapies has yet been shown to be effective intreating DMD.

An alternative pharmacological approach is upregulation therapy.Upregulation therapy is based on increasing the expression ofalternative genes to replace a defective gene and is particularlybeneficial when an immune response is mounted against a previouslyabsent protein. Upregulation of utrophin, an autosomal paralogue ofdystrophin has been proposed as a potential therapy for DMD (Perkins &Davies, Neuromuscul Disord, S1: S78-S89 (2002), Khurana & Davies, NatRev Drug Discov 2:379-390 (2003)). When utrophin is overexpressed intransgenic mdx mice it localizes to the sarcolemma of muscle cells andrestores the components of the dystrophin-associated protein complex(DAPC), which prevents the dystrophic development and in turn leads tofunctional improvement of skeletal muscle. Adenoviral delivery ofutrophin in the dog has been shown to prevent pathology. Commencement ofincreased utrophin expression shortly after birth in the mouse model canbe effective and no toxicity is observed when utrophin is ubiquitouslyexpressed, which is promising for the translation of this therapy tohumans. Upregulation of endogenous utrophin to sufficient levels todecrease pathology might be achieved by the delivery of small diffusiblecompounds.

We have now found a group of compounds which upregulate endogenousutrophin in predictive screens and, thus, may be useful in the treatmentof DMD. According to the invention, we provide use of a compound ofFormula (I)

in whichA₁, A₂, A₃ and A₄, which may be the same or different, represent N orCR₁,X is a divalent group selected from O, S(O)_(n), C═W, NR₄, NC(═O)R₅ andCR₆R₇,

W is O, S, NR₂₀, Y is N or CR₈,

one of R₄, R₅, R₆, R₈, R₉ and NR₂₀ represents -L-R₃, in which L is asingle bond or a linker group,additionally, R₃-R₉, which may be the same or different, independentlyrepresent hydrogen or a substituent andR₂₀ represents hydrogen, hydroxyl, alkyl optionally substituted by aryl,alkoxy optionally substituted by aryl, aryl, CN, optionally substitutedalkoxy, optionally substituted aryloxy, optionally substitute alkanoyl,optionally substituted aroyl, NO₂, NR₃₀R₃₁, in which R₃₀ and R₃₁, whichmay be the same or different, represent hydrogen, optionally substitutedalkyl or optionally substituted aryl; additionally, one of R₃₀ and R₃₁may represent optionally substituted alkanoyl or optionally substitutedaroyl,n represents an integer from 0 to 2,in addition,when an adjacent pair of A₁-A₄ each represent CR₁, then the adjacentcarbon atoms, together with their substituents may form a ring B,when X is CR₆R₇, R₆ and R₇, together with the carbon atom to which theyare attached may form a ring C,when one of A₁-A₄ is CR₁, and R₁ represents COR₁₆, R₁₆ is preferablyalkoxy or NR₁₀R₁₁,or a pharmaceutically acceptable salt thereof,in the manufacture of a medicament for the therapeutic and/orprophylactic treatment of Duchenne muscular dystrophy, Becker musculardystrophy or cachexia.

Compounds of formula I may exist in tautomeric, enantiomeric anddiastereomeric forms, all of which are included within the scope of theinvention.

Certain compounds of formula I are novel. According to the invention, wealso provide those compounds of formula I which are novel, together withprocesses for their preparation, compositions containing them, as wellas their use as pharmaceuticals.

Some of the compounds falling within the scope of formula I are known,as such, but not as pharmaceuticals. According to the invention, weclaim compounds known in the art as such, but not previously describedfor use as pharmaceuticals, as pharmaceuticals.

All of the compounds of formula I may be made by conventional methods.Methods of making heteroaromatic ring systems are well known in the art.In particular, methods of synthesis are discussed in ComprehensiveHeterocyclic Chemistry, Vol. 1 (Eds.: A R Katritzky, C W Rees), PergamonPress, Oxford, 1984 and Comprehensive Heterocyclic Chemistry II: AReview of the Literature 1982-1995 The Structure, Reactions, Synthesis,and Uses of Heterocyclic Compounds, Alan R. Katritzky (Editor), CharlesW. Rees (Editor), E. F. V. Scriven (Editor), Pergamon Pr, June 1996.Other general resources which would aid synthesis of the compounds ofinterest include March's Advanced Organic Chemistry: Reactions,Mechanisms, and Structure, Wiley-Interscience; 5th edition (Jan. 15,2001). Of particular relevance are the synthetic methods discussed in WO2006/044503.

Some general methods of synthesis are as follows.

Benzoxazoles of formula I or pharmaceutically acceptable salts thereofmay be prepared from compounds of formula II.

Reaction Conditions:

-   -   i. R⁹CO₂H (or R⁹COCl), PPA, heat; or R⁹COCl, dioxane, μwave,        then NaOH    -   ii. R⁹COCl, pyridine, rt    -   iii. TsOH, xylenes    -   iv. R⁹CO₂H, HATU, pyridine, DMF    -   v. PPA, heat    -   vi. HATU, DMF, ^(i)Pr₂Net, alkylNH₂, rt

Formation of the benzoxazole I can be carried out in a variety of ways,as illustrated above.

For example, reaction of the compound of formula II with an acylderivative, such as the acid or the acid chloride, and heating in anappropriate solvent and an appropriate temperature in the presence of anacid catalyst, for example polyphosphoric acid. This is illustratedabove as step (i).

The reaction may be carried out in an aprotic solvent, preferably apolar, aprotic solvent, for example tetrahydrofuran, and a temperatureof from −10° C. to +150° C. Generally the reaction may be carried on atthe reflux temperature of the solvent at normal pressure.

Alternatively, the compound of formula II may first be reacted with anexcess of an acyl derivative R⁹COX (where X is for example Cl), suchthat acylation takes place on both oxygen and nitrogen. This can bebrought about by, for example, reaction in pyridine at room temperature(step ii). Ring closure to form the compound of formula II can thenoccur in a subsequent ring closure step in which, for example, thedoubly acylated product is heated in xylenes in the presence of an acidcatalyst such as a sulphonic acid (step iii).

Another illustrative example of formation of a compound of formula I isshown by steps iv and v. First the amine is coupled to an acid using apeptide coupling reagent. Available coupling reagents are well known tothose skilled in the art, and include HBTU, TBTU and HATU. Amideformation in the presence of an appropriate coupling reagent occurs, forexample, in DMF in the presence of a nucleophilic catalyst such aspyridine.

When R¹═CO₂H, this acid may be coupled with an amine as shown by step(vi). Suitable coupling conditions include use of HATU in DMF in thepresence of ^(i)Pr₂NEt, R¹⁶NH₂ at room temperature.

Compounds in which the six membered ring is substituted with an amidederivative are of particular interest. These may be produced from anintermediate amine derivative III.

Reaction Conditions:

-   -   i. As for (i); Scheme 1    -   ii. R¹⁷COCl, pyridine (or NEt₃, DCM); or R⁹CO₂H, HATU, pyridine,        DMF    -   iii. As for (i); Scheme 1    -   iv. SnCl₂, EtOH, heat; or Pd/C, H₂, IMS; or Fe, NH₄Cl,        IMS/water, heat    -   v. R⁹NCO, DCM, rt    -   vi. NaBH(OAc)₃, R¹⁰CHO, DCE, rt    -   vii. R¹⁴SO₂Cl, pyridine, DCM, rt

Intermediate amine III may be synthesised either by using the methodoutlined in scheme 1, step (i) wherein R¹═NH₂, or alternatively, in atwo step process as defined by steps (iii) and (iv) of scheme 2. Nitrosubstituted benzoxazole derivative V is produced from nitro substitutedphenyl derivative W, also in a method analogous to that illustrated byscheme 1, step 1, and then the nitro-benzoxazole derivative V is reducedin a subsequent step to give intermediate amine III. The skilled personis well aware of suitable methods to reduce a nitro group to give anamine. Selective methods for reducing NO₂ to NH₂ include Sn/HCl, orH₂/Pd/C in a suitable solvent, e.g. ethanol at a temperature of from 0°to 80° C. or heating in the presence of iron, NH₄Cl in industrialmethylated spirits/water.

Intermediate amine III can then be coupled as required.

Amide derivatives of formula VI can be produced by coupling amine IIIwith an acyl derivative. This can be achieved by, for example, reactionof an appropriate acid chloride in either pyridine, or in CH₂Cl₂ (stepii).

Sulfonamide derivatives VII can be produced by reaction of amine IIIwith an appropriate sulfonyl chloride in, for example, CH₂Cl₂ in thepresence of pyridine at room temperature.

Amine derivatives VIII can be produced by use of an appropriatereductive amination strategy. Methods of reductive amination are wellknown in the art. They include, for example, reaction of the amine withan appropriate aldehyde and sodium triacetoxyborohydride in1,2-dichloroethane.

Urea derivatives of formula IX can be produced, for example, by reactionof amine III with the appropriate isocyanate, for example, at roomtemperature in CH₂Cl₂.

Benzothiazoles of formula X or pharmaceutically acceptable salts thereofmay be prepared from compounds of formula XI.

Reaction Conditions:

-   -   i. R⁹COCl, pyridine, rt    -   ii. Na₂S, S₈, IMS, heat    -   iii. Fe, NH₄Cl, IMS, heat    -   iv. R¹⁷COCl, pyridine (or NEt₃, DCM); or R¹⁷CO₂H, HATU,        pyridine, DMF

The compounds of formula XI can be converted to the corresponding amideby, for example, reaction with the appropriate acid chloride in pyridine(step (i)), or by using an appropriate peptide coupling reagent. Suchmethods are well known to the person skilled in the art as discussedhereinabove.

The amide can then be converted to the nitro-benzothiazole of formulaXII in a one-pot procedure involving reaction with Na₂S, S₈ at elevatedtemperature in industrial methylated spirit. Nitro derivative XII can bereduced as discussed previously and the resulting primary aminemanipulated in an analogous manner to the primary amine in scheme 2steps (ii), (v), (vi) and (vii).

Reaction conditions:

-   -   i. R⁹CO₂H, PPA, heat; or R⁹COCl, pyridine; then PPA, heat    -   ii. SnCl₂, IMS, heat; or Pd/C, H₂, IMS    -   iii. R¹⁷COCl, pyridine etc (as per Scheme 1)    -   iv. R⁴NH₂, DMSO, base, heat    -   v. Sodium dithionite, THF/water; also see (ii)

Benzimidazoles of formula XII can be produced according to scheme 4.Reaction of a diaminophenyl derivative of formula XIII with an acylderivative, such as an acid or an acid chloride in an appropriatesolvent and at an appropriate temperature in the presence of an acidcatalyst, for example polyphosphoric acid, produces a benzimidazolederivative of formula XII. This is illustrated above as step (i). Thenitro group may then be reduced and manipulated to produce otherfunctionality as discussed hereinabove.

Alternatively, benzimidazoles may be produced by reacting a di-nitrocompound of formula XIV, wherein X represents a leaving group,preferably a halogen such as chlorine or fluorine, with an amine, forexample, in DMSO at elevated temperature in the presence of a base.Subsequent selective reduction of one nitro group using sodiumdithionite in THF/water can then take place to give a diamine of formulaXV. Ring closure to form a benzimidazoles, and manipulation of the nitrogroup can then proceed as illustrated and discussed previously.

Reaction Conditions:

-   -   i. Na₂S hydrate, MeOH, NH₄Cl, water; or Na₂S₂O₄/EtOH; or SnCl₂,        EtOH    -   ii. As for (i), Scheme 1; or R⁹COCl, pyridine; then PPA, heat    -   iii. SnCl₂, EtOH, heat    -   iv. R¹B(OH)₂, Pd(PPh₃)₄, K₂CO₃, dioxane/water, μwave    -   v. R¹⁷COCl, pyridine, rt    -   vi. EtOC(S)SK, pyridine, heat    -   vii. SOCl₂; or POCl₃    -   viii. R³B(OH)₂, Pd(PPh₃)₄, K₂CO₃, solvent    -   ix. PPA, R²CO₂H heat

Benzoxazoles of formula XVI can be made by methods analogous to thosediscussed previously. For example the method illustrated above (ix)involves heating a compound of formula XVII in an appropriate solvent inthe presence of acid catalyst and an appropriate acyl derivative eg acarboxylic acid.

Benzoxazoles of formula XVIII and XIX can be synthesised from theappropriate nitro compound of formula XX. Reduction of the nitrocompound XX gives the corresponding amino alcohol XXI (for example usingSn/HCl, or any of the other appropriate methods well known to the personskilled in the art). Benzoxazole formation via reaction of the aminoalcohol with an appropriate acyl derivative can then be achieved usingany of the methods disclosed hereinabove.

For oxazoles of formula XXIII in which X═Br, a Suzuki coupling reactioncan then be used to give further derivatives. An example of appropriateconditions are R¹B(OH)₂, Pd(PPh₃)₄, K₂CO₃, dioxane/water, μwave, inwhich a benzoxazole of formula XIX results. The person skilled in theart is familiar with Suzuki coupling reactions and could easilymanipulate the conditions to produce a wide variety of compounds.

For oxazoles produced by step (ii) in which X═NO₂, the nitro group canbe reduced to the corresponding amine, using any of the methods wellknown to the person skilled in the art discussed hereinabove. The aminemay then be manipulated using, for example, any of the methods discussedin scheme 2 above, to give, for example, a compound of formula XVIII.

Alternatively, benzoxazoles of formula XVIII can be made, also from acompound of formula XX, via thiocarbamate XXII, which is produced byheating a compound of formula XX with EtOC(S)SK in pyridine. Thecompound of formula XXII can be converted to the chloride of formulaXXIII for example by use of well known reagents such as SOCl₂ or POCl₃.A Suzuki coupling using, for example, conditions illustrated by stepviii above gives a benzoxazole of formula XVIII.

In the above processes it may be necessary for any functional groups,e.g. hydroxy or amino groups, present in the starting materials to beprotected, thus it may be necessary to remove one or more protectivegroups to generate the compound of formula I.

Suitable protecting groups and methods for their removal are, forexample, those described in “Protective Groups in Organic Synthesis” byT. Greene and P.G.M. Wutts, John Wiley and Sons Inc., 1991. Hydroxygroups may, for example, be protected by arylmethyl groups such asphenylmethyl, diphenylmethyl or triphenylmethyl; acyl groups such asacetyl, trichloroacetyl or trifluoroacetyl; or as tetrahydropyranylderivatives. Suitable amino protecting groups include arylmethyl groupssuch as benzyl, (R,S)-α-phenylethyl, diphenylmethyl or triphenylmethyl,and acyl groups such as acetyl, trichloroacetyl or trifluoroacetyl.Conventional methods of deprotection may be used includinghydrogenolysis, acid or base hydrolysis, or photolysis. Arylmethylgroups may, for example, be removed by hydrogenolysis in the presence ofa metal catalyst e.g. palladium on charcoal. Tetrahydropyranyl groupsmay be cleaved by hydrolysis under acidic conditions. Acyl groups may beremoved by hydrolysis with a base such as sodium hydroxide or potassiumcarbonate, or a group such as trichloroacetyl may be removed byreduction with, for example, zinc and acetic acid.

The compounds of formula I, and salts thereof, may be isolated fromtheir reaction mixtures using conventional techniques.

Salts of the compounds of formula I may be formed by reacting the freeacid, or a salt thereof, or the free base, or a salt or derivativethereof, with one or more equivalents of the appropriate base or acid.The reaction may be carried out in a solvent or medium in which the saltis insoluble or in a solvent in which the salt is soluble, e.g. ethanol,tetrahydrofuran or diethyl ether, which may be removed in vacuo, or byfreeze drying. The reaction may also be a metathetical process or it maybe carried out on an ion exchange resin.

Pharmaceutically acceptable salts of the compounds of formula I includealkali metal salts, e.g. sodium and potassium salts; alkaline earthmetal salts, e.g. calcium and magnesium salts; salts of the Group IIIelements, e.g. aluminium salts; and ammonium salts. Salts with suitableorganic bases, for example, salts with hydroxylamine; lower alkylamines,e.g. methylamine or ethylamine; with substituted lower alkylamines, e.g.hydroxy substituted alkylamines; or with monocyclic nitrogenheterocyclic compounds, e.g. piperidine or morpholine; and salts withamino acids, e.g. with arginine, lysine etc, or an N-alkyl derivativethereof; or with an aminosugar, e.g. N-methyl-D-glucamine orglucosamine. The non-toxic physiologically acceptable salts arepreferred, although other salts are also useful, e.g. in isolating orpurifying the product.

Diastereoisomers may be separated using conventional techniques, e.g.chromatography or fractional crystallisation. The various opticalisomers may be isolated by separation of a racemic or other mixture ofthe compounds using conventional, e.g. fractional crystallisation orHPLC, techniques. Alternatively the desired optical isomers may be madeby reaction of the appropriate optically active starting materials underconditions which will not cause racemisation.

Substituents that alkyl may represent include methyl, ethyl, butyl, egsec butyl.

Halogen may represent F, Cl, Br and I, especially Cl.

Examples of substituents that R₃ in the compound of formula I mayrepresent include alkyl, alkoxy or aryl, each optionally substituted byone or more, preferably one to three substituents, R₂, which may be thesame or different.

In addition, when L is single bond, R₃ may represent thioalkyloptionally substituted by alkyl or optionally substituted aryl,

thioaryl, in which the aryl is optionally substituted,

optionally substituted aryl,

hydroxyl,

NO₂,

CN,

NR₁₀R₁₁,

halogen,

SO₂R₁₂,

NR₁₃SO₂R₁₄,

C(═W)R₁₆,

OC(═W)NR₁₀R₁₁

NR₁₅C(═W)R₁₇,

P(═O)OR₄₀R₄₁,

R₁₀, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆, R₁₇, R₄₀ and R₄₁, which may be thesame or which may be the same or different, represent hydrogen, alkyloptionally substituted by optionally substituted aryl, optionallysubstituted aryl,

in addition,

NR₁₀R₁₁ together with the nitrogen to which they are attached may form aring,

R₁₂ may have the same meaning as NR₁₀R₁₁,

when R₁₇ represents NR₁₀R₁₁, that R₁₀ and R₁₁, which may be the same ordifferent, may represent hydrogen, COalkyl and CO optionally substitutedaryl,

R₁₆ and R₁₇, which may be the same or different, may each represent

alkyl substituted by one or more of halogen, alkoxy optionallysubstituted aryl or optionally substituted aryl,

optionally substituted aryloxy,

aryl or NR₁₀R₁₁,

and when R₁₆ or R₁₇ represents NR₁₀R₁₁, one of R₁₀ and R₁₁, mayadditionally represent CO alkyl optionally substituted or COaryloptionally substituted,

and in addition to the definitions shared with R₁₇, R₁₆ may representhydroxy.

Examples of substituents that R₁ and R₂, which may be the same ordifferent, may represent include:

alkyl optionally substituted by one or more halogen, alkoxy oroptionally substituted aryl, thioaryl or aryloxy,

alkoxy optionally substituted by optionally by alkyl or optionallysubstituted aryl,

hydroxyl,

OC(═W)NR₁₀R₁₁

optionally substituted aryl,

thioalkyl optionally substituted by alkyl or optionally substitutedaryl,

thioaryl, in which the aryl is optionally substituted,

NO₂,

CN,

NR₁₀R₁₁,

halogen,

SO₂R₁₂,

NR₁₃SO₂R₁₄,

C(═W)R₁₆,

NR₁₅C(═W)R₁₇,

R₁₀, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆ and R₁₇, which may be the same ordifferent, represent hydrogen, alkyl optionally substituted byoptionally substituted aryl, optionally substituted aryl,

in addition,

NR₁₀R₁₁ together with the nitrogen to which they are attached may form aring,

R₁₂ may have the same meaning as NR₁₀R₁₁,

when R₁₇ represents NR₁₀R₁₁, that R₁₀ and R₁₁, which may be the same ofdifferent, may represent hydrogen, COalkyl and CO optionally substitutedaryl,

R₁₆ may represent hydroxy, alkoxy, or NR₁₀R₁₁,

R₁₇ may represent alkyl substituted by one or more of halogen, alkoxy,optionally substituted aryl or NR₁₀R₁₁,

and when R₁₇ represents NR₁₀R₁₁, that NR₁₀R₁₁ may represent hydrogen,COalkyl and CO optionally substituted aryl.

When L represents a linker group, examples of linker groups that L mayrepresent include:

O, S, (CO)_(n)NR₁₈,

alkylene, alkenylene, alkynylene, each of which may be optionallyinterrupted by one or more of O, S, NR₁₈, or one or more C—C single,double or triple bonds,

a —N—N— single or double bond,

R₁₈ represents hydrogen, alkyl, COR₁₆.

When L is (CO)_(n)NR₁₈, n may represent 0, 1 or 2, when n is 1 or 2, R₁₈preferably represents hydrogen.

Although the scope for variation of R₄, R₅, R₆, R₇ and R₈ is large,preferably R₄, R₅, R₆, R₇ and R₈, represent hydrogen, alkyl oroptionally substituted aryl.

Preferably Y represents N and X represents O, S or NR₄. That ispreferably the compound according to formula I is a benzoxazole, abenzthiazole or a benzimidazole.

Although any one of R₄, R₆, R₈ or R₉ may represent -L-R₃—, in preferredcompounds R₉ represents -L-R₃.

Alkyl may represent any alkyl chain. Alkyl includes straight andbranched, saturated and unsaturated alkyl, as well as cyclic alkyl, suchas cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.However, preferably, when any of the substituents represents alkyl,alkyl is saturated, linear or branched and has from 1 to 10 carbonatoms, preferably from 1 to 8 carbon atoms and more preferably from 1 to6 carbon atoms. When any of the substituents represents alkyl, aparticularly preferred group is cycloalkyl, for example cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.

Aryl may represent any aromatic system. Preferably, in the compounds offormula I, aryl is an aromatic hydrocarbon or a 5 to 10 memberedaromatic heterocycle containing 1 to 4 hetero atoms selected from anoxygen atom, a sulphur atom and a nitrogen atom as a ring constituentbesides carbon. We prefer heterocycles which contain one or twoheteroatoms. Aromatic heterocycles that may be mentioned include furan,thiophene, pyrrole, pyridine.

Particularly preferably, when aryl is an aromatic hydrocarbon, arylrepresents a 6 to 10 membered monocyclic or bicyclic system, for examplephenyl or naphthalene.

Saturated and unsaturated heterocycles that may be mentioned includethose containing 4 to 7 ring atoms, preferably 5 or 6 ring atoms,preferably containing one to two heteroatoms selected from N, S and O.Heterocycles that may be mentioned include pyrrolidine, piperidine,tetrahydrofuran, piperazine and morpholine. N-containing heterocyclesare particularly preferred, eg when NR₁₀R₁₁ forms a heterocyclic ring.

As detailed above, when an adjacent pair of A₁-A₄ each represent CR₁,the adjacent carbon atoms, together with their substituents may form aring B. Also, when X is CR₆R₇, R₆ and R₇, together with the carbon towhich they are attached may form a ring C. Preferably ring B and/or ringC is a saturated or unsaturated 3 to 10 membered carbocylic orheterocyclic ring.

Particularly preferably ring B is benzene ring.

Particularly preferably ring C is a 3-10 membered saturated orunsaturated carbocylic ring.

We particularly prefer compounds in which at least one R₁ representsNR₁₅C(═W)R₁₇, more particularly the group NR₁₅COR₁₇.

We also prefer compounds in which at least one R₁ represents CONR₁₀R₁₁.

For one group of particularly preferred compounds at least one R₁represents an amide group NHCOR₁₇, wherein R₁₇ is selected from:

alkyl C₁-C₆,

alkyl C₁-C₆ substituted by phenyl

alkyl C₁-C₆ substituted by alkoxy C₁-C₆,

haloalkyl C₁-C₆,

perfluoroalkyl C₁-C₆,

phenyl optionally substituted by one or more of halogen, alkyl C₁-C₆,alkoxy C₁-C₆, amino, (alkyl C₁-C₆)amino, di(alkyl C₁-C₆) amino orphenyl,

CH:CH phenyl,

naphthyl, pyridinyl, thiophenyl and furanyl.

We prefer compounds in which one or both of R₁ and R₂ are other than—COOH.

For another group of particularly preferred compounds at least one R₁represents a group NR₁₅CONR₁₀R₁₁, then in which R₁₀ and R₁₁, which maybe the same or different, are selected from optionally substituted aryl,alkyl and COaryl optionally substituted. A particularly preferred groupwhich at least one of R₁ may represent is NHCONHR₁₅ and R₁₅ is selectedfrom phenyl, alkyl C₁ to C₆ and COphenyl optionally substituted by oneor more halogen.

For another group of particularly preferred compounds at least one R₁represents alkyl C1 to C6, optionally substituted by phenyl or a 5 or6-membered saturated or unsaturated heterocycle containing one to twoheteroatoms selected from N, S and O.

For another group of particularly preferred compounds at least one R₁represents COR₁₆ and R₁₆ is alkoxy C₁-C₆, amino, (alkyl C₁-C₆)amino ordi(alkyl C₁-C₆) amino.

For another group of particularly preferred compounds at least one R₁represents:

NO₂,

halogen,

amino or (alkyl C₁-C₆)amino or di(alkyl C₁-C₆) amino in which the alkylC₁ to C₆ is optionally substituted by phenyl or a 5 or 6 memberedsaturated or unsaturated heterocycle,

NHSO₂alkyl C₁-C₆, NHSO₂phenyl,

SO₂alkyl C₁-C₆,

phenyl optionally substituted by C₁ to C₆ alkoxy C1-C6,

a 5-10 membered, saturated or unsaturated, mono- or bi-cyclicheterocycle containing from 1-3 heteroatoms selected from N, S and O.

There is also wide scope for variation of the group R₃. Preferably R₃represents aryl and is optionally substituted by one to threesubstituents, R₂, which may be the same or different.

Particularly preferably, R₃ is a 5-10 membered aromatic mono- orbi-cyclic system, especially a hydrocarbon 5-10 membered aromatic mono-or bi-cyclic system, for example benzene or naphthalene.

Alternatively, the 5-10 membered aromatic mono- or bi-cyclic system, maybe a heterocyclic system containing up to three heteroatoms selectedfrom N, O and S, for example a thiophene, furan, pyridine or pyrrole.

Preferably the substituent(s) R₂ is/are selected from:

alkyl C₁-C₆, optionally substituted by thiophenyl or phenoxy, eachoptionally substituted by halogen,

alkoxy C₁-C₆

phenyl,

thioalkyl C₁-C₆

thiophenyl, optionally substituted by halogen,

NO₂,

CN

NR₁₀R₁₁, in which R₁₀ and R₁₁, which may be the same or differentrepresent hydrogen, alkyl C₁-C₆, or together with the nitrogen to whichthey are attached form a 5 to 7 membered ring which may contain one ormore additional heteroatoms selected from N, O and S,

halogen

SO₂R₁₂, in which R₁₂ represents a 5 to 7 membered ring which may containone or more additional heteroatoms selected from N, O and S

NHCOR₁₇, in which R₁₇ represents

-   -   alkyl C₁-C₆, optionally substituted by:        -   phenyl or halogen, or        -   phenyl optionally substituted by alkoxy C₁-C₆, carboxy or            halogen, or        -   a 5 or 6 membered saturated or unsaturated heterocycle,    -   phenyl or a 5 or 6 membered saturated or unsaturated heterocycle        optionally substituted by halogen, alkoxy C₁ to C₆, carboxy or a        group SO₂NR₁₀R₁₁,

Particularly preferably when R₂ represents NR₁₀R₁₁, NR₁₀R₁₁ representsN-pyrrole, N-piperidine, N′(C₁-C₆) alkyl N piperazine or N-morpholine.

Preferably the linker group L represents:

-   -   —NH.NH—    -   —CH═CH    -   —NCOR₁₆ in which R₁₆ represents phenyl or a 5 or 6 membered        saturated or unsaturated heterocycle optionally substituted by        halogen, alkoxy C1 to C6, carboxy.

A₁-A₄ may represent N or CR₁. Consequently, the benzoxazole six memberedring may contain 1, 2, 3 or 4 nitrogen atoms. Embodiments of theinvention exist in which two of A₁-A₄ represent nitrogen, one of A₁-A₄represents nitrogen and in which all of A₁-A₄ represents CR₁.

In a particularly preferred group of compounds:

A₁, A₂, A₃ and A₄, which may be the same or different, represent N orCR₁,X is a divalent group selected from O, S(O)_(n), C═W, NR₄, NC(═O)R₅ andCR₆R₇,

W is O, S, NR₂₀, Y is N or CR₈,

one of R₄, R₅, R₆, R₈, R₉ and NR₂₀ represents -L-R₃, in which L is asingle bond or a linker group,additionally, R₄-R₉, which may be the same or different, independentlyrepresent hydrogen or a substituent andR₂₀ represents hydrogen, hydroxyl, alkyl optionally substituted by aryl,alkoxy optionally substituted by aryl, aryl, CN, optionally substitutedalkoxy, optionally substituted aryloxy, optionally substitute alkanoyl,optionally substituted aroyl, NO₂, NR₃₀R₃₁, in which R₃₀ and R₃₁, whichmay be the same or different, represent hydrogen, optionally substitutedalkyl or optionally substituted aryl; additionally, one of R₃₀ and R₃₁may represent optionally substituted alkanoyl or optionally substitutedaroyl,n represents an integer from 0 to 2,

R₃ represents alkyl, alkoxy or aryl, each optionally substituted by oneto three substitutents, R₂, which may be the same or different

R₁ and R₂, which may be the same or different, represent:

alkyl optionally substituted by one or more halogen, alkoxy oroptionally substituted aryl, thioaryl or aryloxy,

alkoxy optionally substituted by optionally by alkyl or optionallysubstituted aryl,

hydroxyl,

OC(═W)NR₁₀R₁₁

optionally substituted aryl,

thioalkyl optionally substituted by alkyl or optionally substitutedaryl,

thioaryl, in which the aryl is optionally substituted,

NO₂,

CN,

NR₁₀R₁₁,

halogen,

SO₂R₁₂,

NR₁₃SO₂R₁₄,

C(═W)R₁₆,

NR₁₅C(═W)R₁₇,

R₁₀, R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆ and R₁₇, which may be the same ordifferent, represent hydrogen, alkyl optionally substituted byoptionally substituted aryl, optionally substituted aryl,

in addition,

NR₁₀R₁₁ together with the nitrogen to which they are attached may form aring,

R₁₂ may have the same meaning as NR₁₀R₁₁,

when R₁₇ represents NR₁₀R₁₁, that NR₁₀R₁₁ may represent hydrogen,COalkyl and CO optionally substituted aryl,

R₁₆ may represent hydroxy, alkoxy, or NR₁₀R₁₁,

R₁₇ may represent alkyl substituted by one or more of halogen, alkoxy,optionally substituted aryl or NR₁₀R₁₁,

and when R₁₇ represents NR₁₀R₁₁, that NR₁₀R₁₁ may represent hydrogen,COalkyl and CO optionally substituted aryl,and in addition,when an adjacent pair of A₁-A₄ each represent CR₁, then the adjacentcarbon atoms, together with their substituents may form a ring B,when X is CR₆R₇, R₆ and R₇, together with the carbon atom to which theyare attached may form a ring C,or a pharmaceutically acceptable salt thereof,in the manufacture of a medicament for the therapeutic and/orprophylactic treatment of Duchenne muscular dystrophy, Becker musculardystrophy or cachexia.

We also provide a method for the treatment or prophylaxis of Duchennemuscular dystrophy, Becker muscular dystrophy or cachexia in a patientin need thereof, comprising administering to the patient an effectiveamount of a compound of formula (I) or a pharmaceutical acceptable salt.

The compounds of formula I for use in the treatment of DMD willgenerally be administered in the form of a pharmaceutical composition.

Thus, according to a further aspect of the invention there is provided apharmaceutical composition including preferably less than 80% w/w, morepreferably less than 50% w/w, e.g. 0.1 to 20%, of a compound of formulaI, or a pharmaceutically acceptable salt thereof, as defined above, inadmixture with a pharmaceutically acceptable diluent or carrier.

We also provide a process for the production of such a pharmaceuticalcomposition which comprises mixing the ingredients. Examples ofpharmaceutical formulations which may be used, and suitable diluents orcarriers, are as follows:

for intravenous injection or infusion—purified water or saline solution;

for inhalation compositions—coarse lactose;

for tablets, capsules and dragees—microcrystalline cellulose, calciumphosphate, diatomaceous earth, a sugar such as lactose, dextrose ormannitol, talc, stearic acid, starch, sodium bicarbonate and/or gelatin;

for suppositories—natural or hardened oils or waxes.

When the compound is to be used in aqueous solution, e.g. for infusion,it may be necessary to incorporate other excipients. In particular theremay be mentioned chelating or sequestering agents, antioxidants,tonicity adjusting agents, pH-modifying agents and buffering agents.

Solutions containing a compound of formula I may, if desired, beevaporated, e.g. by freeze drying or spray drying, to give a solidcomposition, which may be reconstituted prior to use.

When not in solution, the compound of formula I preferably is in a formhaving a mass median diameter of from 0.01 to 10 μm. The compositionsmay also contain suitable preserving, stabilising and wetting agents,solubilisers, e.g. a water-soluble cellulose polymer such ashydroxypropyl methylcellulose, or a water-soluble glycol such aspropylene glycol, sweetening and colouring agents and flavourings. Whereappropriate, the compositions may be formulated in sustained releaseform.

The content of compound formula I in a pharmaceutical composition isgenerally about 0.01-about 99.9 wt %, preferably about 0.1-about 50 wt%, relative to the entire preparation.

The dose of the compound of formula I is determined in consideration ofage, body weight, general health condition, diet, administration time,administration method, clearance rate, combination of drugs, the levelof disease for which the patient is under treatment then, and otherfactors.

While the dose varies depending on the target disease, condition,subject of administration, administration method and the like, for oraladministration as a therapeutic agent for the treatment of Duchennemuscular dystrophy in a patient suffering from such a disease is from0.01 mg-10 g, preferably 0.1-100 mg, is preferably administered in asingle dose or in 2 or 3 portions per day.

The potential activity of the compounds of formula I for use in thetreatment of DMD may be demonstrated in the following predictive assayand screens.

1. Luciferase Reporter Assay (Murine H2K Cells)

The cell line used for the screen is an immortalized mdx mouse H2K cellline that has been stably transfected with a plasmid containing ≈5 kbfragment of the Utrophin A promoter including the first untranslatedexon linked to a luciferase reporter gene (see FIG. 1).

Under conditions of low temperature and interferon containing media, thecells remain as myoblasts. These are plated into 96 well plates andcultured in the presence of compound for three days. The level ofluciferase is then determined by cell lysis and reading of the lightoutput from the expressed luciferase gene utilising a plate luminometer.

Example of pharmacological dose response of compounds in the assay isshown in FIG. 2.

2. Mdx Mouse

Data obtained from the ADMET data was prioritised and the compounds withthe best in vitro luciferase activity and reasonable ADMET data wereprioritised for testing in the mdx proof of concept study where theoutcome was to identify whether any of the compounds had the ability toincrease the levels of utrophin protein in dystrophin deficient musclewhen compared to vehicle only dosed control animals.

There were two animals injected with 10 mg/kg of compound administeredip daily for 28 days plus age matched controls. Muscle samples weretaken and processed for sectioning (to identify increases in sarcolemmalstaining of utrophin) and Western blotting (to identify overallincreases in utrophin levels).

FIG. 3 shows an example of TA muscle sections stained with antibodyspecific for mouse utrophin. Comparison to the mdx muscle only injectedwith vehicle shows an increase in the amount of sarcolemmal boundutrophin.

Muscles from the above treated mice were also excised and processed forWestern blotting and stained with specific antibodies (see FIG. 4).Again using muscle dosed with CPD-A shows a significant increase in theoverall levels of utrophin present in both the TA leg muscle and thediaphragm. Both mice exposed to CPD-A (V2 and V3) showed increasedlevels of utrophin expression compared to control.

Positive upregulation data from the first 28 day study were thenrepeated in a further two mouse 28 day study. A total of three differentcompounds have shown in duplicate the ability to increase the level ofutrophin expression in the mdx mouse when delivered daily by ip for 28days. This data demonstrates the ability of the compound when deliveredip causes a significant increase in the levels of utrophin found in themdx muscle and therefore gives us the confidence that this approach willameliorate the disease as all the published data to date demonstratesthat any increase of utrophin levels over three fold has significantfunctional effects on dystrophin deficient muscle.

The H2K/mdx/Utro A reporter cell line maintenance

The H2K/mdx/Utro A reporter cell line was passaged twice a week until≦30% confluent. The cells were grown at 33° C. in the presence of 10%CO₂

To remove the myoblasts for platting, they were incubated withTrypsin/EDTA until the monolayer started to detach.

Growth Medium

DMEM Gibco 41966

20% FCS

1% Pen/Strep

1% glutamine

10 mls Chick embryo extract

Interferon (1276 905 Roche) Add fresh 10 μl/50 mls medium

Luciferase Assay for 96 Well Plates

The H2K/mdx/Utro A reporter cell line cells were plated out into 96 wellplates (Falcon 353296, white opaque) at a density of approximately 5000cells/well in 190 μl normal growth medium. The plates were thenincubated at 33° C. in the presence of 10% CO₂ for 24 hrs.

Compounds were dosed by adding 10 μl of diluted compound to each wellgiving a final concentration of 10 μM. The plates were then incubatedfor a further 48 hrs

Cells were then lysed in situ following the manufacture's protocols(Promega Steady-Glo Luciferase Assay System (E2520). Then counted for 10seconds using a plate luminometer (Victor1420).

Compound Storage

Compounds for screening were stored at −20° C. as 10 mM stocks in 100%DMSO until required.

Injection of Mdx Mice with Compounds

Mdx from a breeding colony were selected for testing. Mice were injecteddaily with either vehicle or 10 mg/kg of compound using theintreperitoneal route (ip). Mice were weighed and compounds diluted in5% DMSO, 0.1% tween in PBS.

Mice were sacrificed by cervical dislocation at desired time points, andmuscles excised for analysis

Muscle Analysis Immunohistochemistry

Tissues for sectioning were dissected, immersed in OCT (BrightCryo-M-Bed) and frozen on liquid nitrogen cooled isopentane. Unfixed 8μM cryosections were cut on a Bright Cryostat, and stored at −80° C.

In readiness for staining, sections were blocked in 5% foetal calf serumin PBS for 30 mins. The primary antibodies were diluted in blockingreagent and incubated on sections for 1.5 hrs in a humid chamber thenwashed three times for 5 mins in PBS. Secondary antibodies also dilutedin blocking reagent, were incubated for 1 hr in the dark in a humidchamber. Finally sections were washed three times 5 mins in PBS andcoverslip Mounted with hydromount. Slides were analysed using a Leicafluorescent microscope.

Results

Biological activity as assessed using the luciferase reporter assay inmurine H2K cells, and is classified as follows:

+ Up to 200% relative to control++ Between 201% and 300% relative to control+++ Between 301% and 400% relative to control++++ Above 401% relative to control

TABLE 1 Compounds made by methods described herein Example Chemical NameActivity 1N-(2-(4-(dimethylamino)phenyl)benzo[d]oxazol-5-yl)isonicotinamide + 2N-(2-(4-fluorophenyl)benzo[d]oxazol-5-yl)furan-2-carboxamide + 32-((4-chlorophenoxy)methyl)-1-methyl-1H-benzo[d]imidazole +++ 42-((4-methoxyphenoxy)methyl)-1H-benzo[d]imidazole ++ 5phenyl(2-phenyl-1H-benzo[d]imidazol-6-yl)methanone + 6N-(2-phenylbenzo[d]oxazol-5-yl)nicotinamide + 73-phenyl-N-(2-phenylbenzo[d]oxazol-5-yl)propanamide + 8N-(2-phenylbenzo[d]oxazol-5-yl)acetamide ++ 9N-(2-phenylbenzo[d]oxazol-5-yl)propionamide ++ 10N-(2-phenylbenzo[d]oxazol-5-yl)butyramide +++ 11N-(2-phenylbenzo[d]oxazol-5-yl)pentanamide ++ 12N-(2-phenylbenzo[d]oxazol-5-yl)isobutyramide ++ 13N-(2-phenylbenzo[d]oxazol-5-yl)furan-2-carboxamide ++ 142-phenylbenzo[d]oxazol-5-amine +++ 152-(4-(trifluoromethyl)phenyl)benzo[d]oxazol-5-amine + 162-(4-(diethylamino)phenyl)benzo[d]oxazol-5-amine ++ 172-(4-(diethylamino)phenyl)benzo[d]oxazol-5-amine + 182-p-tolylbenzo[d]oxazol-5-amine + 194-chloro-N-(2-p-tolylbenzo[d]oxazol-5-yl)benzamide + 204-methoxy-N-(2-p-tolylbenzo[d]oxazol-5-yl)benzamide + 212-(5-nitrobenzo[d]oxazol-2-yl)phenol + 22N-(2-phenylbenzo[d]oxazol-5-yl)isonicotinamide + 234-chloro-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide + 244-methyl-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide + 254-methoxy-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide + 262-methoxy-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide + 274-(dimethylamino)-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide + 283,4-dichloro-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide + 29N-(2-phenylbenzo[d]oxazol-5-yl)-4-(trifluoromethyl)benzamide + 303,5-dichloro-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide + 314-fluoro-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide + 32N-(2-phenylbenzo[d]oxazol-5-yl)biphenyl-4-carboxamide + 332-phenyl-N-(2-phenylbenzo[d]oxazol-5-yl)acetamide + 34N-(2-phenylbenzo[d]oxazol-5-yl)cinnamamide + 35N-(2-phenylbenzo[d]oxazol-5-yl)-1-naphthamide + 36N-(2-phenylbenzo[d]oxazol-5-yl)-2-naphthamide + 37N-(2-phenylbenzo[d]oxazol-5-yl)thiophene-2-carboxamide ++ 382-(5-aminobenzo[d]oxazol-2-yl)phenol +++ 39N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide + 404-chloro-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide + 414-methyl-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide + 424-methoxy-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide + 432-methoxy-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide + 444-(dimethylamino)-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide + 453,4-dichloro-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide + 46N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)-4-(trifluoromethyl)benzamide +47 3,5-dichloro-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide + 484-fluoro-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide + 49N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)biphenyl-4-carboxamide + 502-phenyl-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)acetamide + 513-phenyl-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)propanamide + 52N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)cinnamamide + 53N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)propionamide + 54N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)butyramide + 55N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)pentanamide + 56N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)isobutyramide ++ 57N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)furan-2-carboxamide + 58N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)furan-2-carboxamide + 59N-(2-phenylbenzo[d]oxazol-5-yl)benzamide ++ 60N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)nicotinamide ++ 61N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)isonicotinamide + 62N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)benzamide + 634-chloro-N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)benzamide + 64N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)-4-methylbenzamide + 65N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)-4-methoxybenzamide +66N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)-2-methoxybenzamide +67 N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)-4- ++(dimethylamino)benzamide 683,4-dichloro-N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)benzamide +69 N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)-4- +(trifluoromethyl)benzamide 703,5-dichloro-N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)benzamide +71 N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)-4-fluorobenzamide +72N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)biphenyl-4-carboxamide +73 N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)-2-phenylacetamide++ 74N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)-3-phenylpropanamide +75 N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)propionamide ++ 76N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)butyramide + 77N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)pentanamide ++ 78N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)isobutyramide + 79N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)thiophene-2- +carboxamide 80 3-(5-propylbenzo[d]oxazol-2-yl)benzoic acid + 81N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)nicotinamide + 825-amino-2-(5-aminobenzo[d]oxazol-2-yl)phenol ++ 834-methoxy-N-(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)benzamide + 845-(ethylsulfonyl)-2-phenylbenzo[d]oxazole ++ 852,5-diphenylbenzo[d]oxazole +++ 86 2-phenylnaphtho[1,2-d]oxazole +++ 87N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)isonicotinamide + 88N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)benzamide + 894-chloro-N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)benzamide + 90N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-4-methylbenzamide + 91N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-4-methoxybenzamide + 92N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-2-methoxybenzamide + 93N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-4-(dimethylamino)benzamide +94N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-4-(trifluoromethyl)benzamide +95 3,5-dichloro-N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)benzamide + 96N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-4-fluorobenzamide + 97N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-2-phenylacetamide ++ 98N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-3-phenylpropanamide + 99N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)butyramide ++++ 100N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)pentanamide ++ 101N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)isobutyramide ++++ 102N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)furan-2-carboxamide + 103N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)thiophene-2-carboxamide + 1045-amino-2-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)phenol ++ 1052-(3-methyl-4-nitrophenyl)-1H-benzo[d]imidazole ++++ 1062-(6-nitro-1H-benzo[d]imidazol-2-yl)phenol + 1072-phenylbenzo[d]oxazole-5-carboxylic acid +++ 1082-(4-propylphenyl)benzo[d]oxazole-5-carboxylic acid + 1092-(4-propylphenyl)benzo[d]oxazole-6-carboxylic acid + 1102′-(4-propylphenyl)-2,6′-bibenzo[d]oxazole-6-carboxylic acid + 1115-chloro-2-phenylbenzo[d]oxazole ++ 1126-chloro-2-phenylbenzo[d]oxazole + 113N-(2-p-tolylbenzo[d]oxazol-5-yl)nicotinamide + 114N-(2-p-tolylbenzo[d]oxazol-5-yl)isonicotinamide + 115N-(2-p-tolylbenzo[d]oxazol-5-yl)propionamide ++++ 116N-(2-p-tolylbenzo[d]oxazol-5-yl)butyramide ++++ 117N-(2-p-tolylbenzo[d]oxazol-5-yl)pentanamide +++ 118N-(2-p-tolylbenzo[d]oxazol-5-yl)isobutyramide ++ 119N-(2-p-tolylbenzo[d]oxazol-5-yl)furan-2-carboxamide + 120N-(2-p-tolylbenzo[d]oxazol-5-yl)thiophene-2-carboxamide ++ 121N-(2-(4-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)nicotinamide + 122N-(2-(4-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)isonicotinamide +123 N-(2-(4-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)acetamide ++ 124N-(2-(4-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)propionamide + 125N-(2-(4-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)butyramide + 126N-(2-(4-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)pentanamide + 127N-(2-(4-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)isobutyramide + 128N-(2-(4-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)furan-2-carboxamide +129 5-tert-butyl-2-phenylbenzo[d]oxazole ++++ 1306-nitro-2-phenylbenzo[d]oxazole ++ 1314-(5-chlorobenzo[d]oxazol-2-yl)-N,N-diethylaniline +++ 1324-(6-chlorobenzo[d]oxazol-2-yl)-N,N-diethylaniline ++++ 1332-(5-amino-1H-benzo[d]imidazol-2-yl)phenol + 134N-(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)isonicotinamide + 135N-(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)acetamide +++ 136N-(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)propionamide +++ 137N-(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)butyramide ++ 138N-(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)pentanamide + 139N-(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)isobutyramide ++ 140N-(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)furan-2-carboxamide + 141N-(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)thiophene-2-carboxamide + 1424-(5-tert-butylbenzo[d]oxazol-2-yl)-N,N-diethylaniline ++ 1434-(benzo[d]oxazol-2-yl)-N,N-diethylaniline ++ 144N,N-diethyl-4-(5-(ethylsulfonyl)benzo[d]oxazol-2-yl)aniline + 145N,N-diethyl-4-(5-phenylbenzo[d]oxazol-2-yl)aniline + 146N,N-diethyl-4-(naphtho[1,2-d]oxazol-2-yl)aniline ++ 1472-(pyridin-2-yl)benzo[d]oxazole + 148N-(2-(4-chlorophenyl)-2H-benzo[d][1,2,3]triazol-5-yl)propionamide ++++149 2-(4-(pyrrolidin-1-yl)phenyl)benzo[d]oxazol-5-amine ++ 1502-(4-(piperidin-1-yl)phenyl)benzo[d]oxazol-5-amine ++ 1512-(4-(4-methylpiperazin-1-yl)phenyl)benzo[d]oxazol-5-amine ++ 1522-(4-(diethylamino)phenyl)benzo[d]oxazole-5-carboxylic acid + 1536-nitro-2-phenyloxazolo[5,4-b]pyridine + 1542-propylbenzo[d]oxazol-5-amine + 155 2-phenylbenzo[d]oxazol-6-amine +++156 N-benzyl-2-phenylbenzo[d]oxazol-5-amine +++ 1572-p-tolyloxazolo[5,4-b]pyridine +++ 1582-p-tolyloxazolo[4,5-b]pyridine + 1592-(4-morpholinophenyl)benzo[d]oxazol-5-amine + 1603-methoxy-N-(2-p-tolylbenzo[d]oxazol-5-yl)propanamide ++++ 1615-phenyl-2-p-tolylbenzo[d]oxazole +++ 1622-(4-chlorophenyl)-5-phenylbenzo[d]oxazole + 1632-cyclohexyl-5-nitrobenzo[d]oxazole + 1642-(4-chlorophenyl)-6-nitro-1H-benzo[d]imidazole ++ 165N-(2-benzylbenzo[d]oxazol-5-yl)-2-phenylacetamide + 166N-(2-p-tolyl-1H-benzo[d]imidazol-5-yl)butyramide + 167N-butyl-2-phenylbenzo[d]oxazol-5-amine ++++ 168N-isobutyl-2-phenylbenzo[d]oxazol-5-amine ++++ 1692-phenyloxazolo[5,4-b]pyridin-6-amine + 170N-(2-phenyloxazolo[5,4-b]pyridin-6-yl)butyramide + 1715-nitro-2-(pyridin-2-yl)benzo[d]oxazole + 1725-tert-butyl-2-p-tolylbenzo[d]oxazole ++++ 173 2-p-tolylbenzo[d]oxazole+++ 174 2-(3-(trifluoromethyl)phenyl)benzo[d]oxazol-5-amine + 175N-(2-p-tolyl-1H-benzo[d]imidazol-5-yl)isobutyramide + 176N-butyl-2-p-tolylbenzo[d]oxazole-5-carboxamide ++ 177N-propyl-2-p-tolylbenzo[d]oxazole-5-carboxamide ++++ 178N-(2-(4-chlorophenyl)-1H-benzo[d]imidazol-5-yl)butyramide + 1795-(ethylsulfonyl)-2-p-tolylbenzo[d]oxazole ++++ 1802-(4-chlorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole ++++ 181N-isopropyl-2-p-tolylbenzo[d]oxazole-5-carboxamide +++ 182N-butyl-2-(4-chlorophenyl)benzo[d]oxazol-5-amine +++ 1832-(4-chlorophenyl)-N-isobutylbenzo[d]oxazol-5-amine +++ 184N-benzyl-2-(4-chlorophenyl)benzo[d]oxazol-5-amine + 185N-butyl-2-p-tolylbenzo[d]oxazol-5-amine +++ 186N-isobutyl-2-p-tolylbenzo[d]oxazol-5-amine +++ 187N-benzyl-2-p-tolylbenzo[d]oxazol-5-amine +++ 188N-(2-phenyl-1H-benzo[d]imidazol-5-yl)isobutyramide +++ 1894-nitro-2-p-tolylbenzo[d]oxazole + 190 6-nitro-2-p-tolylbenzo[d]oxazole+++ 191 2-(4-chlorophenyl)-6-nitrobenzo[d]oxazole ++ 1922-p-tolyloxazolo[4,5-c]pyridine + 193N-(2-phenylbenzo[d]oxazol-5-yl)propane-1-sulfonamide ++ 194N-(2-phenyl-1H-benzo[d]imidazol-5-yl)butyramide ++ 195N-(2-(4-chlorophenyl)-1H-benzo[d]imidazol-5-yl)isobutyramide ++ 1962-m-tolylbenzo[d]oxazol-5-amine + 1972-(3-(dimethylamino)phenyl)benzo[d]oxazol-5-amine + 1985-bromo-2-p-tolylbenzo[d]oxazole +++ 1995-(4-methoxyphenyl)-2-p-tolylbenzo[d]oxazole + 200N-(2-m-tolylbenzo[d]oxazol-5-yl)butyramide ++++ 201N-(2-(3-(dimethylamino)phenyl)benzo[d]oxazol-5-yl)butyramide + 202N-(2-m-tolylbenzo[d]oxazol-5-yl)isobutyramide ++++ 203N-(2-(3-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)isobutyramide + 204N-(2-(3-(dimethylamino)phenyl)benzo[d]oxazol-5-yl)isobutyramide ++++ 2052-o-tolylbenzo[d]oxazol-5-amine +++ 2062-(2-chlorophenyl)benzo[d]oxazol-5-amine ++ 207N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)propionamide ++++ 208N-(2-p-tolylbenzo[d]oxazol-5-yl)pivalamide ++ 2092,2,2-trifluoro-N-(2-p-tolylbenzo[d]oxazol-5-yl)acetamide ++ 210N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)pivalamide ++ 211N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-2,2,2-trifluoroacetamide ++212 6-bromo-2-p-tolyloxazolo[5,4-b]pyridine ++ 2132-p-tolylbenzo[d]thiazol-5-amine + 214 2-benzyl-5-nitrobenzo[d]oxazole +215 5,6-dimethyl-2-p-tolylbenzo[d]oxazole ++++ 216N-(2-p-tolylbenzo[d]thiazol-5-yl)butyramide ++++ 217N-(2-p-tolylbenzo[d]thiazol-5-yl)isobutyramide ++++ 2182-p-tolylbenzo[d]oxazole-5-carboxamide ++++ 219N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-N-methylpropionamide +++ 220N-(2-phenylbenzo[d]oxazol-5-yl)propane-2-sulfonamide ++ 221N-(2-phenylbenzo[d]oxazol-5-yl)benzenesulfonamide + 2222-(4-chlorophenyl)-5,6-dimethylbenzo[d]oxazole ++++ 2236-nitro-2-(pyridin-2-yl)benzo[d]oxazole + 2242-(2,4-dichlorophenyl)-5,6-dimethylbenzo[d]oxazole ++++ 225N-(2-(3-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)butyramide + 226N-(2-o-tolylbenzo[d]oxazol-5-yl)isobutyramide ++++ 227N-(2-benzylbenzo[d]oxazol-5-yl)butyramide + 228N-(2-benzylbenzo[d]oxazol-5-yl)isobutyramide + 229N-(2-(2-chlorophenyl)benzo[d]oxazol-5-yl)butyramide +++ 230N-(2-(2-chlorophenyl)benzo[d]oxazol-5-yl)isobutyramide ++++ 231N-(2-(3-chlorophenyl)benzo[d]oxazol-5-yl)isobutyramide ++++ 2322-(3-fluorophenyl)benzo[d]oxazol-5-amine ++++ 2334,4,4-trifluoro-N-(2-p-tolylbenzo[d]oxazol-5-yl)butanamide + 2342-p-tolylbenzo[d]oxazol-4-amine +++ 235N-(2-p-tolylbenzo[d]oxazol-4-yl)butyramide + 236N-(2-p-tolylbenzo[d]oxazol-4-yl)isobutyramide + 2372-p-tolylbenzo[d]oxazol-6-amine ++++ 2382-(2,4-difluorobenzamido)-4,5-dimethylphenyl 2,4-difluorobenzoate + 239N-(2-(3-chlorophenyl)benzo[d]oxazol-5-yl)butyramide + 2401-phenyl-3-(2-phenylbenzo[d]oxazol-5-yl)urea +++ 2411-isopropyl-3-(2-phenylbenzo[d]oxazol-5-yl)urea + 242N-(2-(2-fluorophenyl)benzo[d]oxazol-5-yl)butyramide + 243N-(2-(2-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide +++ 244N-(2-(3-fluorophenyl)benzo[d]oxazol-5-yl)butyramide ++++ 245N-(2-(3-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide +++ 246tert-butyl 3-oxo-3-(2-phenylbenzo[d]oxazol-5-ylamino)propylcarbamate +247 2-(2,4-difluorophenyl)-5,6-dimethylbenzo[d]oxazole ++ 248N-(2-cyclohexylbenzo[d]oxazol-5-yl)isobutyramide ++++ 249N-(2-cyclohexylbenzo[d]oxazol-5-yl)butyramide + 2502-(5-butylpyridin-2-yl)-5-nitrobenzo[d]oxazole + 2512-phenylbenzo[d]thiazol-5-amine +++ 252N-(4-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)phenyl)acetamide +++ 253N-(2-p-tolylbenzo[d]oxazol-5-yl)propane-1-sulfonamide + 2543,3,3-trifluoro-N-(2-p-tolylbenzo[d]oxazol-5-yl)propanamide ++ 255N-(2-(4-chlorophenyl)benzo[d]oxazol-6-yl)isobutyramide ++++ 256N-(2-(4-chlorophenyl)benzo[d]oxazol-6-yl)butyramide ++ 257N-(2-(2,4-dichlorophenyl)benzo[d]oxazol-5-yl)isobutyramide + 258N-(2-(4-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide +++ 259N-(2-p-tolylbenzo[d]oxazol-5-yl)propane-2-sulfonamide + 260N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)propane-1-sulfonamide + 261N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)propane-2-sulfonamide + 2622-(5-butylpyridin-2-yl)-6-nitrobenzo[d]oxazole ++ 2632-(4-chlorophenyl)-N-isopropylbenzo[d]oxazole-5-carboxamide +++ 2642-(4-chlorophenyl)benzo[d]oxazole-5-carboxamide ++++ 265N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)cyclopropanecarboxamide ++++266 N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)cyclobutanecarboxamide +++267 N-(2-phenylbenzo[d]thiazol-5-yl)isobutyramide ++++ 268N-(2-(3,4-dichlorophenyl)benzo[d]oxazol-5-yl)isobutyramide ++++ 2692-(4-chlorophenyl)-5-(4-(ethylsulfonyl)phenyl)benzo[d]oxazole + 270N-(2-(5-chloropyridin-2-yl)benzo[d]oxazol-5-yl)isobutyramide ++++ 271N-(2-(3,5-dichlorophenyl)benzo[d]oxazol-5-yl)isobutyramide ++ 272(S)-2-amino-N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)propanamide +++ 273N-(2-(2,3-dichlorophenyl)benzo[d]oxazol-5-yl)isobutyramide ++++ 2742-(4-chlorophenyl)-N-isopropylbenzo[d]oxazole-5-carbothioamide + 275N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-2-methylpropanethioamide ++276 2-(4-chlorophenyl)benzo[d]thiazol-5-amine ++++ 277N-(2-(4-chlorophenyl)benzo[d]thiazol-5-yl)isobutyramide +++ 2782-(4-chlorophenyl)-N-isopropyl-N-methylbenzo[d]oxazole-5-carboxamide +++279 2-(4-chlorophenyl)-N-methylbenzo[d]oxazole-5-carboxamide +++ 2802-phenethylbenzo[d]oxazol-5-amine ++++ 2812-(4-chlorophenyl)-5-(isopropylsulfonyl)benzo[d]oxazole ++++ 2822-(2-chlorophenyl)benzo[d]thiazol-5-amine ++++ 2832-(3-chlorophenyl)benzo[d]thiazol-5-amine ++++ 2842-(3,4-dichlorophenyl)benzo[d]thiazol-5-amine ++++ 2853-morpholino-N-(2-phenylbenzo[d]oxazol-5-yl)propanamide + 2862-(benzo[d][1,3]dioxol-5-yl)-5-nitrobenzo[d]oxazole +++ 287 methyl4-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)benzoate + 2885-bromo-2-(4-chlorophenyl)benzo[d]oxazole ++++ 2894-(5-chlorobenzo[d]oxazol-2-yl)aniline ++++ 2904-(6-chlorobenzo[d]oxazol-2-yl)aniline +++ 2912-(4-chlorophenyl)-5-(4-morpholinophenyl)benzo[d]oxazole ++ 2922-(4-chlorophenyl)-5-(3-(ethylthio)phenyl)benzo[d]oxazole ++ 2932-(3-chlorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole ++++ 294N-(2-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)phenyl)acetamide + 295N-(2-(2-chlorophenyl)benzo[d]thiazol-5-yl)isobutyramide ++++ 296N-(2-(3-chlorophenyl)benzo[d]thiazol-5-yl)isobutyramide ++++ 297N-(2-(3,4-dichlorophenyl)benzo[d]thiazol-5-yl)isobutyramide ++++ 2982-(2-Chlorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole ++ 2992-(benzo[d][1,3]dioxol-5-yl)benzo[d]oxazol-5-amine ++ 300N-(2-(benzo[d][1,3]dioxol-5-yl)benzo[d]oxazol-5-yl)isobutyramide +++ 3012-(3,4-diChlorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole ++ 302N-(2-phenethylbenzo[d]oxazol-5-yl)isobutyramide + 303N-(2-(2,3-dichlorophenyl)benzo[d]thiazol-5-yl)isobutyramide +++ 3042-(2,3-diChlorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole + 3052-(4-chlorophenyl)-5-(6-methoxypyridin-3-yl)benzo[d]oxazole ++ 3062-(4-chlorophenyl)-5-(6-methoxypyridin-3-yl)benzo[d]oxazole + 3072-(2,3-dichlorophenyl)benzo[d]thiazol-5-amine +++ 3082-(1-phenylethyl)benzo[d]oxazol-5-amine + 309N-(2-(1-phenylethyl)benzo[d]oxazol-5-yl)isobutyramide + 3102-(4-chlorophenyl)-5,6-methylenedioxybenzoxazole +++ 311N-(2-(2,5-dichlorophenyl)benzo[d]oxazol-5-yl)isobutyramide + 3122-(4-chlorophenyl)benzo[d]oxazole-5-sulfonic acid + 3133-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)benzoic acidd + 3142-(4-chlorophenyl)-5-(6-chloropyridin-3-yl)benzo[d]oxazole + 3152-(4-chlorophenyl)-5-(6-fluoropyridin-3-yl)benzo[d]oxazole + 3162-(4-chlorophenyl)-5-(6-morpholinopyridin-3-yl)benzo[d]oxazole + 317N-(4-(5-chlorobenzo[d]oxazol-2-yl)phenyl)acetamide +++ 318N-(4-(5-chlorobenzo[d]oxazol-2-yl)phenyl)isobutyramide ++ 319N-(4-(5-chlorobenzo[d]oxazol-2-yl)phenyl)thiophene-2-carboxamide + 320N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-N-methylisobutyramide ++ 3215-tert-butyl-2-(4-chlorophenyl)benzo[d]oxazole ++++ 3222-(4-chlorophenyl)-N-isobutyl-N-methylbenzo[d]oxazol-5-amine + 323N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-3-methoxypropanamide ++++ 3242-(3,4-dichlorophenyl)-6-nitrobenzo[d]oxazole ++ 3252-(4-chlorophenyl)benzo[d]oxazole-5-sulfonamide ++++ 3265-chloro-2-(4-chlorophenyl)-6-nitrobenzo[d]oxazole +++ 3272-(4-chlorophenyl)-5-(6-methoxypyridin-2-yl)benzo[d]oxazole + 3283-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)aniline ++++ 3294-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)aniline ++++ 3305-chloro-2-(pyridin-4-yl)benzo[d]oxazole + 3316-chloro-2-(pyridin-4-yl)benzo[d]oxazole + 332N-(4-(6-chlorobenzo[d]oxazol-2-yl)phenyl)acetamide +++ 333N-(4-(6-chlorobenzo[d]oxazol-2-yl)phenyl)isobutyramide ++ 334N-(4-(6-chlorobenzo[d]oxazol-2-yl)phenyl)thiophene-2-carboxamide + 3352-(4-chlorophenyl)-N,N-diisobutylbenzo[d]oxazol-5-amine + 3364-(5-bromobenzo[d]oxazol-2-yl)aniline ++++ 3374-amino-N-(4-(5-bromobenzo[d]oxazol-2-yl)phenyl)benzamide + 3385-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)pyridin-2-amine ++++ 3392-(4-chlorophenyl)-5-phenyl-1H-indole + 340N-(2-(2-chloro-4-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide ++++ 341N-(2-(2-chloro-6-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide + 342N-(2-(3-chloro-2-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide ++++ 343N-(2-(4-chloro-2-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide ++++ 344N-(2-(2-chloro-5-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide + 345N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-3,3,3-trifluoropropanamide +++346 N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)cyclopentanecarboxamide +347 N-(5-chloro-2-(4-chlorophenyl)benzo[d]oxazol-6-yl)isobutyramide ++348 5-nitro-2-(4-(trifluoromethoxy)phenyl)benzo[d]oxazole ++ 349N-(2-(tetrahydro-2H-pyran-4-yl)benzo[d]oxazol-5-yl)isobutyramide + 3502-(4-(trifluoromethoxy)phenyl)benzo[d]oxazol-5-amine ++ 351N-(2-(3,4-dichlorophenyl)benzo[d]oxazol-5-yl)cyclopropanecarboxamide++++ 352N-(2-(3,4-dichlorophenyl)benzo[d]oxazol-5-yl)-3,3,3-trifluoropropanamide++++ 353N-(2-(4-chlorophenyl)benzo[d]oxazol-6-yl)cyclopropanecarboxamide ++ 354N-(2-(2,3-dichlorophenyl)benzo[d]oxazol-6-yl)isobutyramide +++ 355N-(2-(4-(trifluoromethoxy)phenyl)benzo[d]oxazol-5-yl)isobutyramide + 3564-(5-(4-chlorophenyl)benzo[d]oxazol-2-yl)aniline + 3572-morpholino-5-nitrobenzo[d]oxazole + 358N-(5-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)pyridin-2-yl)acetamide + 359N-(4-(5-bromobenzo[d]oxazol-2-yl)phenyl)acetamide ++++ 3602-morpholinobenzo[d]oxazol-5-amine + 3612-(3,4-chlorophenyl)-5,6-methylenedioxybenzoxazole + 362(S)—N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)pyrrolidine-2-carboxamide++ 363N-(2-(2,3-dichlorophenyl)benzo[d]oxazol-5-yl)-3,3,3-trifluoropropanamide++++ 364 N-(2-cyclopentylbenzo[d]oxazol-5-yl)isobutyramide + 365N-(4-(5-acetamidobenzo[d]oxazol-2-yl)phenyl)acetamide + 3662-(furan-2-yl)-5-nitrobenzo[d]oxazole + 367N-(4-(2-(4-chlorophenyl)-1H-indol-5-yl)phenyl)acetamide + 368N-(2-(2-chloro-3-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)isobutyramide +369 2-(3,4-dichlorophenyl)benzo[d]oxazol-6-amine ++++ 370N-(2-(3,4-dichlorophenyl)benzo[d]oxazol-6-yl)isobutyramide ++++ 3712-(benzo[d][1,3]dioxol-5-yl)-5-chloro-6-nitrobenzo[d]oxazole +++ 372N-(4-(5-(4-chlorophenyl)benzo[d]oxazol-2-yl)phenyl)acetamide + 373N-(2-(naphthalen-2-yl)benzo[d]oxazol-5-yl)acetamide ++++ 374N-(2-(4-acetamidophenyl)benzo[d]oxazol-5-yl)isobutyramide + 375N-(2-phenyl-1H-indol-6-yl)isobutyramide + 3762,3-dichloro-N-(2-(2,3-dichlorophenyl)benzo[d]oxazol-5-yl)benzamide +377 (S)—N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)-2- +++(methylamino)propanamide 378 N-(1-methyl-1H-indol-6-yl)isobutyramide +379 2-(4-chlorobenzylthio)-5-nitrobenzo[d]oxazole + 3802-(4-chlorobenzylthio)benzo[d]oxazol-5-amine + 381N2-(4-chlorobenzyl)benzo[d]oxazole-2,5-diamine + 3822-(4-methylbenzylthio)-5-nitrobenzo[d]oxazole + 383N-(2-(4-chlorobenzylthio)benzo[d]oxazol-5-yl)isobutyramide + 384N-(2-(naphthalen-2-yl)benzo[d]oxazol-5-yl)isobutyramide +++ 385N-(2-(naphthalen-2-yl)benzo[d]oxazol-5-yl)thiophene-2-carboxamide + 386ethyl 2-(4-chlorophenyl)benzo[d]oxazol-5-ylcarbamate + 387N-(1-benzyl-1H-indol-6-yl)isobutyramide + 3885-nitro-2-(thiophen-2-yl)benzo[d]oxazole + 389N-(1-methyl-2-phenyl-1H-indol-6-yl)isobutyramide + 3905-(ethylsulfonyl)-2-(naphthalen-2-yl)benzo[d]oxazole +++ 3912-(3-chloro-2-fluorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole ++ 3922-cyclohexyl-5-(ethylsulfonyl)benzo[d]oxazole + 3932-(5-chloropyridin-2-yl)-5-(ethylsulfonyl)benzo[d]oxazole ++ 3942-(benzo[d][1,3]dioxol-5-yl)-5-(ethylsulfonyl)benzo[d]oxazole ++++ 3955-chloro-2-(4-(methylsulfonyl)phenyl)benzo[d]oxazole ++ 396N-(2-phenylbenzofuran-5-yl)isobutyramide ++++ 3972-(benzo[d][1,3]dioxol-5-yl)-5-chlorobenzo[d]oxazol-6-amine +++ 398N-(2-(benzo[d][1,3]dioxol-5-yl)-5-chlorobenzo[d]oxazol-6-yl)isobutyramide +399 2-(4-chlorophenyl)-6-(methylthio)benzo[d]thiazole +++ 4002-(4-chlorophenyl)-5-(methylsulfonyl)benzo[d]oxazole ++ 4012-(biphenyl-4-yl)benzo[d]oxazol-5-amine +++ 4022-(quinolin-2-yl)benzo[d]oxazol-5-amine +++ 4032-(quinolin-3-yl)benzo[d]oxazol-5-amine +++ 4042-(6-methoxynaphthalen-2-yl)benzo[d]oxazol-5-amine ++ 4052-(6-bromonaphthalen-2-yl)benzo[d]oxazol-5-amine + 4062-(4-chlorophenyl)-6-(methylsulfonyl)benzo[d]thiazole ++++ 407S-2-(4-chlorophenyl)benzo[d]oxazol-5-yl ethanethioate + 4082-phenyl-5-(3′,3′,3′-trifluoropropanamido)benzofuran + 4092-(4-chlorophenyl)naphtho[1,2-d]oxazole ++++ 410N-(2-(naphthalen-1-yl)benzo[d]oxazol-5-yl)isobutyramide + 411N-(2-(biphenyl-4-yl)benzo[d]oxazol-5-yl)isobutyramide + 412N-(2-(6-methoxynaphthalen-2-yl)benzo[d]oxazol-5-yl)isobutyramide + 413N-(2-(6-bromonaphthalen-2-yl)benzo[d]oxazol-5-yl)isobutyramide + 4142-(4′-chlorophenyl)-5-isobutyramido-benzofuran + 415N-(2-(quinolin-3-yl)benzo[d]oxazol-5-yl)isobutyramide ++++ 416N-(2-(quinolin-2-yl)benzo[d]oxazol-5-yl)isobutyramide ++++ 4171-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)propan-1-one ++++ 4185-(ethylsulfonyl)-2-(5-methylthiophen-2-yl)benzo[d]oxazole ++++ 419N-(2-(furan-2-yl)benzo[d]oxazol-5-yl)isobutyramide ++++ 4201-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)ethanone ++++ 4212-(4-cyclohexylphenyl)benzo[d]oxazol-5-amine ++++ 4225-(ethylsulfonyl)-2-(quinolin-2-yl)benzo[d]oxazole ++++ 4235-(ethylsulfonyl)-2-(quinolin-3-yl)benzo[d]oxazole ++++ 4242-(6-bromonaphthalen-2-yl)-5-(ethylsulfonyl)benzo[d]oxazole + 4252-(4-cyclohexylphenyl)-5-(ethylsulfonyl)benzo[d]oxazole + 4262-(biphenyl-4-yl)-5-(ethylsulfonyl)benzo[d]oxazole + 4275-(ethylsulfonyl)-2-(naphthalen-1-yl)benzo[d]oxazole + 4285-amino-2-(5,6-dichlorobenzo[d]oxazol-2-yl)phenol +++ 4295-(ethylsulfonyl)-2-(thiophen-2-yl)benzo[d]oxazole ++ 430N-(2-(4-cyclohexylphenyl)benzo[d]oxazol-5-yl)isobutyramide + 4315-(ethylsulfonyl)-2-(6-fluoronaphthalen-2-yl)benzo[d]oxazole + 4322-(benzo[b]thiophen-5-yl)-5-(ethylsulfonyl)benzo[d]oxazole ++++ 433N-(4-(5,6-dimethylbenzo[d]oxazol-2-yl)-3-hydroxyphenyl)acetamide ++ 4342-(3,4-dichlorophenyl)-5-(isopropylsulfonyl)benzo[d]oxazole +++ 435N-(4-(5,6-dimethylbenzo[d]oxazol-2-yl)-3-hydroxyphenyl)acetamide ++ 4365-(ethylsulfonyl)-2-(3-methylthiophen-2-yl)benzo[d]oxazole ++ 4372-(5-(ethylsulfonyl)benzo[d]oxazol-2-yl)naphthalen-1-ol ++++ 4382-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-5-(ethylsulfonyl)benzo[d]oxazole +439 2-(4′-chlorophenyl)-5-(N,N-diethylsulfonamidyl)-benzoxazole + 4404-(5,6-dichlorobenzo[d]oxazol-2-yl)aniline ++++ 4415-(ethylsulfonyl)-2-(5-methylfuran-2-yl)benzo[d]oxazole +++ 442N-(4-(naphtho[1,2-d]oxazol-2-yl)phenyl)isobutyramide +++ 4435-(ethylsulfonyl)-2-(4-methylthiophen-2-yl)benzo[d]oxazole ++++ 4445-(ethylsulfonyl)-2-(5,6,7,8-tetrahydronaphthalen-2-yl)benzo[d]oxazole+++ 445 2-(benzofuran-5-yl)-5-(ethylsulfonyl)benzo[d]oxazole ++++ 4462-(4′-chlorophenyl)-5-(1′-hydroxyethyl)-benzoxazole ++++ 4475-Amino-2-(5-(ethylsulfonyl)benzo[d]oxazol-2-yl)phenol ++ 4482-(Naphthalen-2-yl)-5-(trifluoromethoxy)benzo[d]oxazole ++++ 4492-(Naphthalen-2-yl)benzo[d]oxazole-5-carboxylic acid ++++ 4502-(Naphthalen-2-yl)benzo[d]oxazole ++++ 4515-tert-Butyl-2-(naphthalen-2-yl)benzo[d]oxazole + 4525,6-Difluoro-2-(naphthalen-2-yl)benzo[d]oxazole ++++ 4531-(2′-(3″,4″-Dichlorophenyl)benzo[d]oxazol-5′-yl)ethanone ++++ 454N-(4-(Benzo[d]oxazol-2-yl)phenyl)isobutyramide ++++ 455 Methyl2-(4-chlorophenyl)benzo[d]oxazol-5-yl(ethyl)phosphinate ++++ 4562-(3′,4′-Dichlorophenyl)-5-(1′-hydroxyethyl)-benzoxazole ++++ 4572-(4-Chlorophenyl)-6-methylbenzo[d]oxazole ++++ 4585-Methyl-2-(naphthalen-2-yl)benzo[d]oxazole ++++

TABLE 2 Compounds made by analogues methods to those described herein,or by literature methods known or adapted by the persons skilled in theart. 459 Chemical Name Activity 4602-(4-((4-chlorophenylthio)methyl)phenyl)-1H-benzo[d]imidazole + 4612-((2,4-dichlorophenoxy)methyl)-1H-benzo[d]imidazole +++ 4622,6-dichloro-N-(5-methylbenzo[d]thiazol-2-ylcarbamoyl)benzamide + 4632-(thiophen-2-yl)-1H-benzo[d]imidazole + 464N-(3-(1H-benzo[d]imidazol-2-yl)phenyl)benzamide + 4651-(2-chlorobenzyl)-2-((2,4-dichlorophenoxy)methyl)-1H-benzo[d]imidazole +466 1-(2-methylbenzo[d]oxazol-6-yl)-3-phenylurea + 4671-methyl-3-(2-methylbenzo[d]oxazol-6-yl)urea + 4682-chloro-N-(2-methylbenzo[d]oxazol-6-ylcarbamoyl)benzamide + 4692-(4-chlorophenyl)-5-(piperidin-1-ylmethyl)benzo[d]oxazole + 4702-(4-methoxyphenyl)-1H-benzo[d]imidazole ++ 4712-(phenoxymethyl)-1H-benzo[d]imidazole ++ 4721-methyl-2-(4-nitrophenyl)-1H-benzo[d]imidazole + 4732-((4-methoxyphenoxy)methyl)-1H-benzo[d]imidazole ++ 4741-methyl-2-(phenoxymethyl)-1H-benzo[d]imidazole + 4754-(1H-benzo[d]imidazol-2-yl)aniline + 4762,2′-(1,4-phenylene)bis(1H-benzo[d]imidazol-6-amine) + 4772-(4-nitrophenyl)benzo[d]oxazole + 478 4-(benzo[d]oxazol-2-yl)aniline ++479 5-(benzo[d]thiazol-2-yl)-2-methylaniline ++ 4802-(3,4-dichlorophenyl)benzo[d]oxazol-5-amine ++ 4812-(4-ethylphenyl)benzo[d]oxazol-5-amine ++ 4822-(3,5-dimethylphenyl)benzo[d]oxazol-5-amine + 4832-(benzo[d]thiazol-2-yl)phenol + 4845-amino-2-(benzo[d]oxazol-2-yl)phenol ++ 4854-(5,6-dimethylbenzo[d]oxazol-2-yl)aniline ++ 4864-(benzo[d]oxazol-2-yl)-N,N-dimethylaniline + 4872-(4-aminophenyl)-1H-benzo[d]imidazol-6-amine + 4882-(4-chlorophenyl)benzo[d]oxazol-5-amine ++ 4892-(3-chlorophenyl)benzo[d]oxazol-5-amine ++ 4902-(4-aminophenyl)-1-methyl-1H-benzo[d]imidazol-5-amine + 4912-(4-(dimethylamino)phenyl)benzo[d]oxazol-5-amine ++ 4925-nitro-2-phenylbenzo[d]oxazole ++ 493N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-2-(thiophen-2-yl)acetamide + 494N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-3,4-dimethoxybenzamide + 4952-((4-chlorophenoxy)methyl)-1H-benzo[d]imidazole + 4964-(5-aminobenzo[d]oxazol-2-yl)phenol ++ 497N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)benzamide + 4984-(1H-benzo[d]imidazol-2-yl)-N,N-dimethylaniline + 4992-(methoxymethyl)-1H-benzo[d]imidazole + 500N-(2-(1H-benzo[d]imidazol-2-yl)phenyl)-2,4-dichlorobenzamide + 501N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-2-phenylacetamide + 5023-(5-ethylbenzo[d]oxazol-2-yl)aniline ++ 503N-(3-(1H-benzo[d]imidazol-2-yl)phenyl)acetamide + 504N-(3-(1H-benzo[d]imidazol-2-yl)phenyl)thiophene-2-carboxamide + 5055-methyl-2-(4-nitrophenyl)benzo[d]oxazole ++ 5064-(6-methylbenzo[d]oxazol-2-yl)aniline + 5072-(2-fluorophenyl)-1H-benzo[d]imidazole ++ 5082-(furan-2-yl)-5-nitro-1H-benzo[d]imidazole + 509N,N-dimethyl-4-(5-nitro-1H-benzo[d]imidazol-2-yl)aniline ++ 5102-(furan-2-yl)-1H-benzo[d]imidazol-5-amine dihydrochloride + 511N-(2-(1H-benzo[d]imidazol-2-yl)phenyl)-4-(pyrrolidin-1-ylsulfonyl)benzamide +512 2-(4-methoxyphenyl)benzo[d]oxazol-5-amine + 513N-(3-(benzo[d]thiazol-2-yl)phenyl)acetamide + 5142-(3-chlorophenyl)-1H-benzo[d]imidazole + 5152-(3,4-dimethoxyphenyl)benzo[d]oxazol-5-amine ++ 5162-(4-(piperidin-1-ylsulfonyl)phenyl)benzo[d]thiazole ++ 517N-(2-(2,4-dichlorophenyl)benzo[d]oxazol-5-yl)acetamide ++ 5184-(5,7-dichlorobenzo[d]oxazol-2-yl)aniline ++ 519N-(2-(3-chloro-4-methoxyphenyl)benzo[d]oxazol-5-yl)acetamide ++ 5202-(3,4-dimethoxyphenyl)-5-nitro-1H-benzo[d]imidazole + 5212-(3,4-dimethoxyphenyl)-1-methyl-1H-benzo[d]imidazole + 5222-(2-methoxyphenyl)benzo[d]thiazole + 5232-(4-chloro-3-nitrophenyl)benzo[d]thiazole + 5242-(2-chloro-5-nitrophenyl)benzo[d]thiazole + 5252-(4-fluorophenyl)-5-nitrobenzo[d]oxazole + 5262-(3-chloro-4-methylphenyl)benzo[d]oxazol-5-amine ++ 5272-(2-chloro-4-methylphenyl)benzo[d]oxazol-5-amine ++ 5282-((4-methoxyphenoxy)methyl)-1-methyl-1H-benzo[d]imidazole ++ 529N-(4-(5,7-dimethylbenzo[d]oxazol-2-yl)phenyl)acetamide ++ 5302-((1H-benzo[d]imidazol-2-yl)methylthio)-5-phenyl-1,3,4-oxadiazole + 5312-(p-tolyloxymethyl)-1H-benzo[d]imidazole ++ 5324-(5-methyl-1H-benzo[d]imidazol-2-yl)aniline + 5335-nitro-2-m-tolylbenzo[d]oxazole ++ 534N-(2-(furan-2-yl)-1H-benzo[d]imidazol-5-yl)acetamide + 5352-(4-methoxyphenyl)-1H-benzo[d]imidazol-5-amine ++ 536N-(2-(furan-2-yl)-1H-benzo[d]imidazol-5-yl)-4-methylbenzenesulfonamide +537 2-(3,4-dimethoxyphenyl)-5-nitrobenzo[d]oxazole + 538N-(3-(6-methyl-1H-benzo[d]imidazol-2-yl)phenyl)furan-2-carboxamide + 5395-chloro-2-(3-methyl-4-nitrophenyl)benzo[d]oxazole + 540N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)benzo[d][1,3]dioxole-5-carboxamide +541 2-(4-chlorophenyl)-1-methyl-1H-benzo[d]imidazole ++ 542N-(5-(benzo[d]thiazol-2-yl)-2-methoxyphenyl)acetamide ++ 5432-(4-(methylthio)phenyl)-1H-benzo[d]imidazole ++ 5442-(4-aminophenyl)benzo[d]oxazol-6-amine ++ 5452-(4-(6-methylbenzo[d]thiazol-2-yl)phenylcarbamoyl)benzoic acid + 546(Z)-1-(benzo[d]thiazol-2-yl)-4-(1-(cyclopropylamino)ethylidene)-3-methyl-1H- +pyrazol-5(4H)-one 547 (E)-2-styryl-1H-benzo[d]imidazole +++ 5482-((2,5-dimethylphenoxy)methyl)-1H-benzo[d]imidazole + 5492-(4-ethoxyphenyl)benzo[d]oxazol-5-amine + 5504-amino-2-(5-aminobenzo[d]thiazol-2-yl)phenol + 5514-amino-2-(5-ethylbenzo[d]oxazol-2-yl)phenol + 5522-(2-phenylhydrazinyl)benzo[d]thiazole + 5534-(5-ethylbenzo[d]oxazol-2-yl)aniline ++++ 5542-(5-methyl-1H-benzo[d]imidazol-2-yl)aniline +++ 555N-(6-ethoxybenzo[d]thiazol-2-yl)benzamide + 556N-(4-(6-acetamido-5-chloro-1H-benzo[d]imidazol-2-yl)phenyl)acetamide +557 4-(4-(1H-benzo[d]imidazol-2-yl)phenoxy)aniline ++++ 5582-(biphenyl-4-yl)-1H-benzo[d]imidazole + 5594-amino-2-(5,6-dimethylbenzo[d]oxazol-2-yl)phenol +++ 5602-(4-chlorophenyl)-1H-benzo[d]imidazol-5-amine +++ 5612-(thiophen-2-yl)-1H-naphtho[2,3-d]imidazole +++ 562N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)furan-2-carboxamide +++ 5632-(ethylthio)benzo[d]thiazol-6-amine ++ 564N-(4-(6-methylbenzo[d]oxazol-2-yl)phenyl)isobutyramide + 5655-amino-2-(5-isopropylbenzo[d]oxazol-2-yl)phenol +++ 5663-(5-chlorobenzo[d]oxazol-2-yl)-2-methylaniline + 567N-(benzo[d]thiazol-2-yl)-2-chloro-4-methylbenzamide + 568N-(5-(1H-benzo[d]imidazol-2-yl)-2-methylphenyl)-2,2,2-trifluoroacetamide+++ 569 2-(2-fluorophenyl)benzo[d]oxazol-5-amine +++ 5702-butyl-5-(ethylsulfonyl)benzo[d]oxazole + 5715-(ethylsulfonyl)-2-propylbenzo[d]oxazole + 5722-ethyl-5-(ethylsulfonyl)benzo[d]oxazole + 5735-(ethylsulfonyl)benzo[d]oxazole + 5745-(ethylsulfonyl)benzo[d]oxazole-2-thiol + 575N-(3-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)phenyl)acetamide ++++ 5761-(2-tert-butyl-1H-indol-5-yl)-3-ethylurea + 5772-(naphthalen-1-yl)benzo[d]oxazol-5-amine + 5782-(4-chlorophenyl)-5-(propylsulfonyl)benzo[d]oxazole + 5792-(4-chlorophenyl)benzo[d]oxazol-6-ol ++++ 580N-(4-(5-Methyl-1H-benzo[d]imidazol-2-yl)phenyl)furan-2-carboxamide +++581 Phenyl (2-phenyl-1H-benzo[d]imidazol-6-yl)methanone + 5822-(4-Methoxyphenyl)benzo[d]thiazole ++++ 5832-(4-Methoxyphenyl)benzo[d]oxazole +++ 5842-(4-Methoxyphenyl)-6-nitrobenzo[d]oxazole +++ 585N-(4-(1H-Benzo[d]imidazol-2-yl)phenyl)thiophene-2-carboxamide ++++ 5862-(4-Methoxyphenyl)-5-nitro-1H-benzo[d]imidazole ++ 587N-(4-(1H-Benzo[d]imidazol-2-yl)phenyl)tetrahydrofuran-2-carboxamide +++588 1-Methyl-2-p-tolyl-1H-benzo[d]imidazole +++ 589N-(4-(Benzo[d]oxazol-2-yl)phenyl)acetamide +++ 5904-(4,6-Dimethylbenzo[d]oxazol-2-yl)aniline ++++ 591N-(4-(1H-Benzo[d]imidazol-2-yl)phenyl)acetamide +++ 5925-(Benzo[d]thiazol-2-yl)-2-chloroaniline ++++ 5934-(5-Tert-butylbenzo[d]oxazol-2-yl)aniline +++ 5943-(Benzo[d]thiazol-2-yl)phenol ++++ 5952-(2,4-Dichlorophenyl)benzo[d]thiazole ++ 5965-(Benzo[d]thiazol-2-yl)-2-methoxyphenol ++++ 5975-(Benzo[d]thiazol-2-yl)-2-methoxyaniline +++ 5982-(3-Chlorophenyl)benzo[d]oxazol-6-amine +++ 5992-(3-Methyl-4-nitrophenyl)benzo[d]thiazole ++++ 6002-(3-Methoxyphenyl)-1H-benzo[d]imidazole ++ 6014-(Benzo[d]thiazol-2-yl)aniline +++ 602 3-(Benzo[d]thiazol-2-yl)aniline+++ 603 2-(3,4-Dimethylphenyl)benzo[d]oxazol-5-amine +++ 6046-Nitro-2-phenyl-1H-benzo[d]imidazole +++ 6055-Methyl-2-(4-nitrophenyl)-1H-benzo[d]imidazole +++ 6062-(3-Methoxyphenyl)benzo[d]thiazole +++ 6072-(3-Methyl-4-nitrophenyl)benzo[d]oxazole ++++ 6082-(Benzo[d][1,3]dioxol-5-yl)benzo[d]thiazole ++++ 6094-(5-Sec-butylbenzo[d]oxazol-2-yl)aniline +++ 6105-Amino-2-(5,6-dimethylbenzo[d]oxazol-2-yl)phenol ++++ 6116-Methyl-2-(4-(trifluoromethyl)phenyl)benzo[d]oxazole +++ 6125-Methyl-2-(thiophen-2-yl)benzo[d]oxazole ++ 6132-p-Tolyl-1H-benzo[d]imidazole +++ 6142-(Benzo[d][1,3]dioxol-5-yloxy)-N-(benzo[d]thiazol-2-yl)acetamide + 6151-ethyl-2-methyl-N-phenyl-1H-benzo[d]imidazole-5-carboxamide ++++ 616N-(benzo[d]thiazol-2-yl)-2-bromobenzamide ++++ 6172-(benzo[d]thiazol-2-ylthio)-1-(piperidin-1-yl)ethanone ++++ 618N-(benzo[d][1,3]dioxol-5-yl)-3-chlorobenzo[b]thiophene-2-carboxamide++++ 619 5-(benzo[d]oxazol-2-yl)-2-methoxyaniline ++++ 6205-(1H-benzo[d]imidazol-2-yl)-2-methylaniline ++++ 6213-chloro-N-(2-fluorophenyl)benzo[b]thiophene-2-carboxamide ++++ 6223-(5-chlorobenzo[d]oxazol-2-yl)aniline ++++ 623N-(3-(5,6-dimethylbenzo[d]oxazol-2-yl)phenyl)furan-2-carboxamide ++++624 N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-3-methylbutanamide ++++ 6255-(5-ethylbenzo[d]oxazol-2-yl)-2-methylaniline ++++ 626N-(benzo[d]thiazol-2-yl)benzofuran-2-carboxamide ++++ 6272-chloro-5-(5,7-dimethylbenzo[d]oxazol-2-yl)aniline ++++ 6283-amino-N-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[e]thieno[2,3- ++++b]pyridine-2-carboxamide 6292-bromo-N-(6-fluorobenzo[d]thiazol-2-yl)benzamide ++++ 6303-(5-methoxybenzo[d]oxazol-2-yl)aniline ++++ 631N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)-2-methylbutanamide ++++ 6326-methyl-2-(5-methyl-1H-benzo[d]imidazol-2-yl)thieno[2,3-b]pyridin-3-amine++++ 633 2-(phenoxymethyl)benzo[d]thiazole +++ 6341-ethyl-2-methyl-5-phenyl-1H-benzo[d]imidazole +++ 6352-methyl-5-(6-methylbenzo[d]oxazol-2-yl)aniline +++ 6362-chloro-5-(5-methylbenzo[d]oxazol-2-yl)aniline +++ 6371-(benzo[d]thiazol-2-yl)-3-p-tolylurea +++ 638N-(4-(6-methylbenzo[d]thiazol-2-yl)phenyl)nicotinamide +++ 6392-(quinolin-2-yl)benzo[d]thiazole +++ 6402-(4-methoxybenzylthio)-1H-benzo[d]imidazole +++ 6412-chloro-N-(4-(oxazolo[4,5-b]pyridin-2-yl)phenyl)benzamide +++ 642N-(3-(5-ethylbenzo[d]oxazol-2-yl)phenyl)acetamide +++ 6434-(6-methylbenzo[d]thiazol-2-yl)phenol +++ 644N-(3-(5-methylbenzo[d]oxazol-2-yl)phenyl)propionamide +++ 6452-(3-fluoro-4-methoxybenzylthio)-1-methyl-1H-benzo[d]imidazole +++ 6464-chloro-3-(5,6-dimethylbenzo[d]oxazol-2-yl)aniline +++ 6473-(benzo[d]thiazol-2-yl)-N-(pyridin-4-ylmethyl)aniline +++ 648N-(1H-benzo[d]imidazol-2-yl)-2-methylbenzamide +++ 6492-(4-bromo-3-methylphenyl)benzo[d]oxazol-5-amine +++ 6503-amino-4,6-dimethyl-N-m-tolylthieno[2,3-b]pyridine-2-carboxamide +++651 N-(4-(benzo[d]thiazol-2-yl)phenyl)isobutyramide +++ 652N-(6-methylbenzo[d]thiazol-2-yl)furan-2-carboxamide +++ 6535-(1H-benzo[d]imidazol-2-yl)-2-chloroaniline +++ 6542-(4H-1,2,4-triazol-3-ylthio)-N-(4-(6-methylbenzo[d]thiazol-2- +++yl)phenyl)acetamide 6554-(4-(1H-benzo[d]imidazol-2-yl)phenylcarbamoyl)phenyl acetate +++ 6563,5,6-trimethyl-N-(pyridin-4-ylmethyl)benzofuran-2-carboxamide +++ 6572-ethoxy-N-(4-(6-methylbenzo[d]thiazol-2-yl)phenyl)acetamide +++ 658N-(6-fluorobenzo[d]thiazol-2-yl)thiophene-2-carboxamide +++ 6591-(1H-benzo[d]imidazol-2-yl)-3-methyl-4-phenyl-1H-pyrazol-5-amine +++660 3-ethoxy-N-(4-(6-methylbenzo[d]thiazol-2-yl)phenyl)propanamide +++661 N-(4-(benzo[d]thiazol-2-yl)phenyl)cyclopropanecarboxamide +++ 662N-(4-(5-methylbenzo[d]oxazol-2-yl)phenyl)acetamide +++ 663N-(2-bromo-4-methylphenyl)-2-(1H-indol-3-yl)-2-oxoacetamide +++ 6644-(6-methylbenzo[d]thiazol-2-yl)aniline ++ 665N-phenethylbenzofuran-2-carboxamide ++ 6664-chloro-N-((1-methyl-1H-benzo[d]imidazol-2-yl)methyl)aniline ++ 667N-(4-(benzo[d]thiazol-2-yl)phenyl)propionamide ++ 668N-(2-m-tolylbenzo[d]oxazol-5-yl)propionamide ++ 669N-(1-methyl-1H-benzo[d]imidazol-2-yl)benzimidamide ++ 6704-methyl-N-(1-methyl-1H-benzo[d]imidazol-5-yl)benzamide ++ 671N-(benzo[d]thiazol-2-yl)-5-bromo-2-chlorobenzamide ++ 672N-(4-(6-methylbenzo[d]oxazol-2-yl)phenyl)thiophene-2-carboxamide ++ 6733-amino-N-(2-fluorophenyl)-6,7-dihydro-5H-cyclopenta[e]thieno[2,3- ++b]pyridine-2-carboxamide 674(3-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl)methanol ++ 6752-(4-methoxyphenyl)-5-methylbenzo[d]oxazole ++ 6764-ethoxy-N-((1-methyl-1H-benzo[d]imidazol-2-yl)methyl)aniline ++ 677N-(2-chloro-5-(5-methylbenzo[d]oxazol-2-yl)phenyl)furan-2-carboxamide ++678N-(4-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)benzo[d]oxazol-2-++ amine 679 N-(1H-benzo[d]imidazol-2-yl)-3-chlorobenzamide ++ 680N-(4-(benzo[d]thiazol-2-yl)phenyl)tetrahydrofuran-2-carboxamide ++ 6811-(2-(benzo[d]oxazol-2-ylamino)-4,6-dimethylpyrimidin-5-yl)ethanone ++682 N-(4-methylpyrimidin-2-yl)benzo[d]oxazol-2-amine ++ 683N-(6-(N,N-dimethylsulfamoyl)benzo[d]thiazol-2-yl)thiophene-2-carboxamide++ 6845-bromo-N-(4-hydroxy-3-(5-methylbenzo[d]oxazol-2-yl)phenyl)nicotinamide++ 6852-(1H-1,2,4-triazol-3-ylthio)-N-(4-(benzo[d]thiazol-2-yl)phenyl)acetamide++ 686 5-(5-methoxybenzo[d]oxazol-2-yl)-2-methylaniline ++ 687N-(6-(N-methylsulfamoyl)benzo[d]thiazol-2-yl)thiophene-2-carboxamide ++6882-chloro-N-(4-(5-methylbenzo[d]thiazol-2-yl)phenyl)-5-(4H-1,2,4-triazol-4-++ yl)benzamide 689 N-(2-fluorophenyl)-2-(1H-indol-3-yl)-2-oxoacetamide++ 670N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(1H-indol-3-yl)-2-oxoacetamide++

EXPERIMENTAL

HPLC-UV-MS was performed on a Gilson 321 HPLC with detection performedby a Gilson 170 DAD and a Finnigan AQA mass spectrometer operating inelectrospray ionisation mode. The HPLC column used is a PhenomenexGemini C18 150×4.6 mm. Preparative HPLC was performed on a Gilson 321with detection performed by a Gilson 170 DAD. Fractions were collectedusing a Gilson 215 fraction collector. The preparative HPLC column usedis a Phenomenex Gemini C18 150×10 mm and the mobile phase isacetonitrile/water.

¹H NMR spectra were recorded on a Bruker instrument operating at 300MHz. NMR spectra were obtained as CDCl₃ solutions (reported in ppm),using chloroform as the reference standard (7.25 ppm) or DMSO-D₆ (2.50ppm). When peak multiplicities are reported, the following abbreviationsare used s (singlet), d (doublet), t (triplet), m (multiplet), br(broadened), dd (doublet of doublets), dt (doublet of triplets), td(triplet of doublets). Coupling constants, when given, are reported inHertz (Hz).

Column chromatography was performed either by flash chromatography(40-65 μm silica gel) or using an automated purification system (SP1™Purification System from Biotage). Reactions in the microwave were donein an Initiator 8™ (Biotage).

The abbreviations used are DMSO (dimethylsulfoxide), HATU(O-(7-azabenzotriazol-1yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate), HCl (hydrochloric acid), MgSO₄ (magnesiumsulfate), NaOH (sodium hydroxide), Na₂CO₃ (sodium carbonate), NaHCO₃(sodium bicarbonate), STAB (sodium triacetoxyborohydride), THF(tetrahydrofuran).

Method 1A (Compounds I) 2-Phenylbenzo[d]oxazol-5-amine

To polyphosphoric acid at 110° C. were added simultaneously2,4-diaminophenol dihydrochloride (7.88 g, 40 mmol) and benzoic acid(4.88 g, 40 mmol). The resulting mixture was then heated to 180° C. for3 h. The solution was then poured into water. The resulting precipitatewas collected by filtration and washed with saturated sodium bicarbonatesolution. The crude product was recrystallised from ethanol/water toafford 8.15 g (97%) of the title compound (LCMS RT=5.17 min, MH⁺ 211.1)

¹H NMR (DMSO): 8.15-8.12 (2H, m), 7.60-7.56 (3H, m), 7.42 (1H, d, J=8.7Hz), 6.89 (1H, d, J=2.1 Hz), 6.68 (1H, dd, J 8.6 2.2 Hz), 5.12 (2H, s)

All compounds below were prepared following the same general method andpurified either by trituration, recrystallisation or columnchromatography.

2-(4-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-amine

LCMS RT=8.98 min, MH⁺ 279.0; ¹H NMR (DMSO): 8.26 (2H, d, J 8.2 Hz), 7.88(2H, d, J 8.3 Hz), 7.40 (1H, d, J 8.7 Hz), 6.84 (1H, d, J 2.1 Hz), 6.66(1H, dd, J 8.8 2.2 Hz), 5.13 (2H, s)

2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-amine

LCMS RT=8.98 min, MH⁺ 282.2; ¹H NMR (DMSO): 7.89 (2H, d, J 9.1 Hz), 7.30(1H, d, J 8.5 Hz), 6.80-6.76 (3H, m), 6.54 (1H, dd, J 8.8 2.2 Hz), 4.99(2H, s), 3.42 (2H, q, J 7.1 Hz), 1.14 (3H, q, J 7.1 Hz)

2-(Pyridin-3-yl)benzo[d]oxazol-5-amine

LCMS RT=6.42 min, MH⁺ 212.2; ¹H NMR (DMSO): 9.29 (1H, d, J 1.9 Hz), 8.77(1H, dd, J 4.8 1.4 Hz), 8.48-8.44 (1H, m), 7.62 (1H, dd, J 9.0 4.8 Hz),7.46 (1H, d, J 8.8 Hz), 6.91 (1H, d, J 2.0 Hz), 6.71 (1H, dd, J 8.7 2.1Hz), 5.18 (2H, s)

2-(5-Nitrobenzo[d]oxazol-2-yl)phenol

LCMS RT=6.94 min; ¹H NMR (DMSO): 10.91 (1H, s), 8.74 (1H, d, J 2.3 Hz),8.37 (1H, dd, J 9.0 2.4 Hz), 8.11-8.04 (2H, m), 7.60-7.55 (1H, m),7.18-7.08 (2H, m)

2-(5-Aminobenzo[d]oxazol-2-yl)phenol

LCMS RT=6.08 min, MH⁺ 227.2; ¹H NMR (DMSO): 11.46 (1H, s), 8.02 (1H, dd,J 7.8 1.6 Hz), 7.58-7.53 (2H, m), 7.18-7.10 (2H, m), 6.96 (1H, d, J 2.1Hz), 6.77 (1H, dd, J 8.7 2.2 Hz), 5.29 (2H, s)

3-(5-Propylbenzo[d]oxazol-2-yl)benzoic acid

LCMS RT=4.58 min, MH⁺ 282.1; ¹H NMR (DMSO): 13.44 (1H, s), 8.78 (1H, s),8.47 (1H, d, J=8.0 Hz), 8.22 (1H, d, J=8.4 Hz), 7.84-7.74 (2H, m), 7.70(1H, s), 7.35 (1H, d, J=9.0 Hz), 2.78-2.73 (2H, m), 1.71 (2H, q, J=7.6Hz), 0.98 (3H, d, J=7.2 Hz)

5-Amino-2-(5-aminobenzo[d]oxazol-2-yl)phenol

LCMS RT=5.24 min, MH⁺ 242.2; ¹H NMR (DMSO): 11.40 (1H, s), 7.63 (1H, d,J 8.6 Hz), 7.40 (1H, d, J 8.7 Hz), 6.83 (1H, d, J 2.1 Hz), 6.63 (1H, dd,J 8.6 2.3 Hz), 6.31 (1H, d, J 8.4 2.2 Hz), 6.22 (1H, d, J 1.9 Hz), 6.05(2H, s), 5.15 (2H, s)

5-(Ethylsulfonyl)-2-phenylbenzo[d]oxazole

LCMS RT=5.94 min, MH⁺ 288.1; ¹H NMR (DMSO): 8.32 (1H, d, J 1.3 Hz), 8.26(2H, dd, J 6.4 1.6 Hz), 8.10 (1H, d, J 8.5 Hz), 7.97 (1H, dd, J 8.5 1.7Hz), 7.72-7.64 (3H, m), 3.43-3.38 (2H, m), 1.14 (3H, t, J 7.4 Hz)

2,5-Diphenylbenzo[d]oxazole

LCMS RT=9.41 min, MH⁺ 271.9; ¹H NMR (DMSO): 8.26-8.23 (2H, m), 8.08 (1H,d, J 1.3 Hz), 7.89 (1H, d, J 8.5 Hz), 7.77-7.72 (3H, m), 7.68-7.61 (3H,m), 7.51 (2H, t, J 7.7 Hz), 7.43-7.38 (1H, m)

2-Phenylnaphtho[1,2-d]oxazole

LCMS RT=8.75 min, MH⁺ 246.2; ¹H NMR (DMSO): 8.48 (1H, d, J=8.1 Hz),8.32-8.27 (2H, m), 8.14 (1H, d, J 8.1 Hz), 8.01 (2H, s), 7.78-7.72 (1H,m), 7.68-7.60 (4H, m)

2-Phenylbenzo[d]oxazole-5-carboxylic acid

LCMS RT=4.41 min, MH⁺ 240.1; ¹H NMR (DMSO): 13.00 (1H, br), 8.33 (1H,dd, J 1.6 0.5 Hz), 8.26-8.23 (2H, m), 8.06 (1H, dd, J 8.6 1.7 Hz), 7.91(1H, dd, J 8.5 0.5 Hz), 7.72-7.62 (3H, m)

2-(4-Propylphenyl)benzo[d]oxazole-5-carboxylic acid

¹H NMR (DMSO): 13.10 (1H, br), 8.30 (1H, dd, J 1.5 0.4 Hz), 8.15 (2H, d,J 8.3 Hz), 8.04 (1H, dd, J 8.6 1.7 Hz), 7.88 (1H, d, J 8.5 Hz), 7.47(2H, d, J 8.4 Hz), 2.68 (2H, t, J 8.0 Hz), 1.70-1.62 (2H, m), 0.93 (3H,t, J 7.5 Hz)

2-(4-Propylphenyl)benzo[d]oxazole-6-carboxylic acid

¹H NMR (DMSO): 13.10 (1H, br), 8.27 (1H, dd, J 1.5 0.5 Hz), 8.16 (2H, d,J 8.3 Hz), 8.02 (1H, dd, J 8.3 1.5 Hz), 7.88 (1H, dd, J 8.3 0.5 Hz),7.48 (2H, d, J 8.4 Hz), 2.68 (2H, t, J 8.0 Hz), 1.72-1.58 (2H, m), 0.93(3H, t, J 7.5 Hz)

5-Chloro-2-phenylbenzo[d]oxazole

LCMS RT=8.61 min, MH⁺ 230.1; ¹H NMR (DMSO): 8.21 (2H, dd, J 7.6 1.4 Hz),7.94 (1H, d, J 2.1 Hz), 7.86 (1H, d, J 8.7 Hz), 7.72-7.60 (3H, m), 7.49(1H, dd, J 8.7 2.1 Hz)

6-Chloro-2-phenylbenzo[d]oxazole

LCMS RT=9.00 min, MH⁺ 230.1; ¹H NMR (DMSO): 8.22-8.18 (2H, m), 8.02 (1H,d, J 1.9 Hz), 7.84 (1H, d, J 8.5 Hz), 7.70-7.60 (3H, m), 7.48 (1H, dd, J8.5 2.0 Hz)

5-Tert-butyl-2-phenylbenzo[d]oxazole

LCMS RT=9.82 min, MH⁺ 252.0; ¹H NMR (DMSO): 7.72-7.70 (4H, m), 7.59 (2H,dt, J 7.6 1.0 Hz), 7.46-7.40 (2H, m), 1.38 (9H, s)

6-Nitro-2-phenylbenzo[d]oxazole

LCMS RT=7.30 min; ¹H NMR (DMSO): 8.77-8.76 (1H, m), 8.34 (1H, d, J 8.8Hz), 8.27 (2H, d, J 7.7 Hz), 8.05 (1H, d, J 8.8 Hz), 7.80-7.65 (3H, m)

4-(5-Chlorobenzo[d]oxazol-2-yl)-N,N-diethylaniline

LCMS RT=10.17 min, MH⁺ 301.1; ¹H NMR (DMSO): 8.03 (2H, d, J 8.9 Hz),7.82-7.76 (2H, m), 7.40 (1H, dd, J 8.6 2.0 Hz), 6.89 (2H, d, J 8.9 Hz)

4-(6-Chlorobenzo[d]oxazol-2-yl)-N,N-diethylaniline

LCMS RT=10.28 min, MH⁺ 301.0; ¹H NMR (DMSO): 7.95 (2H, d, J 9.1 Hz),7.87 (1H, d, J 1.7 Hz), 7.67 (1H, d, J 8.4 Hz), 7.38 (1H, dd, J 8.4 2.1Hz), 6.83 (2H, d, J 9.1 Hz), 3.45 (4H, q, J 7.2 Hz), 1.15 (6H, t, J 7.1Hz)

4-(5-Tert-butylbenzo[d]oxazol-2-yl)-N,N-diethylaniline

LCMS RT=13.81 min, MH⁺ 323.2; ¹H NMR (DMSO): 7.94 (2H, d, J 9.3 Hz),7.66 (1H, d, J 1.5 Hz), 7.58 (1H, d, J 8.6 Hz), 7.36 (1H, dd, J 8.6 1.9Hz), 6.82 (2H, d, J 9.2 Hz), 3.44 (4H, q, J 7.0 Hz), 1.35 (9H, s), 1.15(6H, t, J 7.1 Hz)

4-(Benzo[d]oxazol-2-yl)-N,N-diethylaniline

LCMS RT=10.50 min, MH⁺ 267.0; ¹H NMR (DMSO): 7.97 (2H, d, J 9.1 Hz),7.71-7.64 (2H, m), 7.36-7.30 (2H, m), 6.82 (2H, d, J 9.2 Hz), 3.44 (4H,q, J 7.0 Hz), 1.15 (6H, t, J 7.1 Hz)

N,N-Diethyl-4-(5-(ethylsulfonyl)benzo[d]oxazol-2-yl)aniline

LCMS RT=7.45 min, MH⁺ 358.9; ¹H NMR (DMSO): 8.13 (1H, dd, J 1.3 0.4 Hz),8.00 (2H, d, J 9.1 Hz), 7.95 (1H, dd, J 8.1 0.4 Hz), 7.83 (1H, dd, J 8.41.8 Hz), 6.85 (2H, d, J=9.2 Hz), 3.50-3.39 (6H, m), 1.23-1.04 (9H, m)

N,N-Diethyl-4-(5-phenylbenzo[d]oxazol-2-yl)aniline

LCMS RT=15.22 min, MH⁺ 343.1; ¹H NMR (DMSO): 7.99 (2H, d, J 8.9 Hz),7.93 (1H, s), 7.77-7.71 (3H, m), 7.60 (1H, d, J 8.3 Hz), 7.52-7.46 (2H,m), 7.40-7.35 (1H, m), 6.84 (2H, d, J 9.0 Hz), 3.44 (4H, q, J 7.0 Hz),1.15 (6H, t, J 7.1 Hz)

N,N-Diethyl-4-(naphtho[1,2-d]oxazol-2-yl)aniline

LCMS RT=11.211 min, MH⁺ 317.1; ¹H NMR (DMSO): 8.41 (1H, d, J 8.3 Hz),8.12-8.02 (3H, m), 7.94-7.86 (2H, m), 7.72-7.66 (1H, m), 7.60-7.55 (1H,m), 6.85 (2H, d, J 9.0 Hz), 3.44 (4H, q, J 7.0 Hz), 1.15 (6H, t, J 7.1Hz)

2-(Pyridin-2-yl)benzo[d]oxazole

LCMS RT=5.68 min, MH⁺ 197.0; ¹H NMR (DMSO): 8.87 (1H, d, J 4.4 Hz), 8.41(1H, d, J 8.0 Hz), 8.14 (1H, dt, J 7.8 1.5 Hz), 7.93 (2H, t, J 7.4 Hz),7.73-7.69 (1H, m), 7.60-7.50 (2H, m)

2-(4-(Piperidin-1-yl)phenyl)benzo[d]oxazol-5-amine

LCMS RT=6.95 min, MH⁺ 206.1; ¹H NMR (DMSO): 7.92 (2H, d, J 9.0 Hz), 7.32(1H, d, J 9.0 Hz), 7.05 (2H, d, J 9.0 Hz), 6.80 (1H, d, J 2.1 Hz), 6.58(1H, dd, J 8.0 2.0 Hz), 5.01 (2H, s), 1.60 (6H, m)

2-(4-(4-Methylpiperazin-1-yl)phenyl)benzo[d]oxazol-5-amine

LCMS RT=5.34 min, MH⁺ 309.1; ¹H NMR (DMSO): 7.94 (2H, d, J 9.0 Hz), 7.33(1H, d, J 9.0 Hz), 7.08 (2H, d, J 9.0 Hz), 6.80 (1H, d, J 2.1 Hz), 6.58(1H, dd, J 8.0 2.0 Hz), 5.03 (2H, s), 2.60-2.57 (4H, m), 2.45-2.42 (4H,m), 2.23 (3H, s)

2-(4-(Diethylamino)phenyl)benzo[d]oxazole-5-carboxylic acid

¹H NMR (DMSO): 13.00 (1H, br), 8.17 (1H, d, J 1.5 Hz), 7.99 (2H, d, J9.0 Hz), 7.94 (1H, dd, J 8.5 1.7 Hz), 7.77 (1H, d, J 8.4 Hz), 6.84 (2H,d, J 9.1 Hz), 3.45 (4H, q, J 7.0 Hz), 1.15 (6H, t, J 7.0 Hz)

2-Propylbenzo[d]oxazol-5-amine

LCMS RT=6.81 min, MH⁺ 177.2; ¹H NMR (DMSO): 7.26 (1H, d, J 8.6 Hz), 6.76(1H, d, J 2.2 Hz), 6.57 (1H, dd, J 8.6 2.2 Hz), 4.98 (2H, s), 2.80 (2H,t, J 7.3 Hz), 1.81-1.70 (2H, m), 0.96 (3H, t, J 7.4 Hz)

2-p-Tolyloxazolo[5,4-b]pyridine

LCMS RT=6.72 min, MH⁺ 211.1; ¹H NMR (DMSO): 8.38 (1H, dd, J 5.0 1.5 Hz),8.26 (1H, dd, J 7.9 1.6 Hz), 8.14 (2H, d, J 8.2 Hz), 7.53-7.45 (3H, m),2.44 (3H, s)

2-p-Tolyloxazolo[4,5-b]pyridine

LCMS RT=6.12 min, MH⁺ 211.1; ¹H NMR (DMSO): 8.54 (1H, dd, J 4.9 1.4 Hz),8.23 (1H, dd, J 8.2 1.4 Hz), 8.16 (2H, d, J 8.2 Hz), 7.59-7.44 (3H, m),2.44 (3H, s)

2-(4-Morpholinophenyl)benzo[d]oxazol-5-amine

LCMS RT=5.52 min, MH⁺ 295.8; ¹H NMR (DMSO): 7.97 (2H, d, J 9.0 Hz), 7.33(1H, d, J 9.0 Hz), 7.09 (2H, d, J 9.0 Hz), 6.81 (1H, d, J 2.1 Hz), 6.59(1H, dd, J 8.0 2.0 Hz), 5.04 (2H, s), 3.77-3.74 (4H, m), 3.29-3.24 (4H,m)

5-Phenyl-2-p-tolylbenzo[d]oxazole

LCMS RT=10.00 min, MH⁺ 286.1; ¹H NMR (DMSO): 8.12 (2H, d, J 8.5 Hz),8.06 (1H, d, J 1.8 Hz), 7.86 (1H, d, J 8.6 Hz), 7.77-7.70 (3H, m),7.53-7.37 (5H, m), 2.43 (3H, s)

2-(4-Chlorophenyl)-5-phenylbenzo[d]oxazole

LCMS RT=10.54 min, MH⁺ 306.0; ¹H NMR (DMSO): 8.24 (2H, d, J 8.6 Hz),8.09 (1H, d, J 1.8 Hz), 7.89 (1H, d, J 8.6 Hz), 7.77-7.70 (5H, m),7.53-7.34 (3H, m)

2-Cyclohexyl-5-nitrobenzo[d]oxazole

LCMS RT=7.90 min, MH⁺ 247.3; ¹H NMR (CDCl₃): 8.62 (1H, d, J 2.2 Hz),8.33 (1H, dd, J 8.9 2.3 Hz), 7.63 (1H, d, J 8.9 Hz), 3.11-3.01 (1H, m),2.27-2.21 (2H, m), 1.98-1.92 (2H, m), 1.84-1.71 (3H, m), 1.57-1.37 (3H,m)

5-Tert-butyl-2-p-tolylbenzo[d]oxazole

LCMS RT=10.53 min, MH⁺ 266.1; ¹H NMR (DMSO): 8.08 (2H, d, J 8.2 Hz),7.78 (1H, d, J 1.6 Hz), 7.68 (1H, d, J 8.6 Hz), 7.48 (1H, dd, J 8.7 2.0Hz), 7.43 (2H, d, J 8.0 Hz), 2.42 (3H, s), 1.37 (9H, s)

2-p-Tolylbenzo[d]oxazole

LCMS RT=7.82 min, MH⁺ 210.1; ¹H NMR (DMSO): 8.11 (2H, d, J 8.2 Hz),7.81-7.76 (2H, m), 7.46-7.40 (4H, m), 2.42 (3H, s)

2-(3-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-amine

LCMS RT=6.39 min, MH⁺ 279.0; ¹H NMR (DMSO): 8.41 (1H, d, J 8.0 Hz), 8.37(1H, s), 7.98 (1H, d, J 8.0 Hz), 7.84 (1H, t, J 8.0 Hz), 7.46 (1H, d, J8.9 Hz), 6.91 (1H, d, J 1.9 Hz), 6.72 (1H, d, J 8.6 2.0 Hz), 5.18 (2H,s)

5-(Ethylsulfonyl)-2-p-tolylbenzo[d]oxazole

LCMS RT=6.46 min, MH⁺ 302.0; ¹H NMR (DMSO): 8.28 (1H, d, J 1.6 Hz), 8.14(2H, d, J 8.2 Hz), 8.06 (1H, d, J 8.6 Hz), 7.94 (1H, dd, J 8.6 1.7 Hz),7.47 (2H, d, J 8.1 Hz), 3.42-3.34 (2H, m), 2.44 (3H, s), 1.12 (3H, t, J7.3 Hz)

2-(4-Chlorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=6.63 min, MH⁺ 322.1; ¹H NMR (CDCl₃): 8.39 (1H, d, J 1.7 Hz),8.27 (2H, d, J 8.7 Hz), 8.00 (1H, dd, J 8.5 1.8 Hz), 7.80 (1H, d, J 8.5Hz), 7.60 (2H, d, J 8.6 Hz), 3.23 (2H, q, J 7.6 Hz), 1.36 (3H, t, J 7.4Hz)

4-Nitro-2-p-tolylbenzo[d]oxazole

LCMS RT=6.97 min, MH⁺ 255.0; ¹H NMR (DMSO): 8.27 (1H, dd, J 8.1 0.8 Hz),8.23 (1H, dd, J 8.2 0.8 Hz), 8.18 (2H, d, J 8.2 Hz), 7.65 (1H, t, J 8.2Hz), 7.49 (2H, d, J 8.0 Hz), 2.45 (3H, s)

6-Nitro-2-p-tolylbenzo[d]oxazole

LCMS RT=7.83 min, MH⁺ 255.0; ¹H NMR (DMSO): 8.74 (1H, d, J 2.2 Hz), 8.33(1H, dd, J 8.7 2.2 Hz), 8.17 (2H, d, J 8.2 Hz), 8.02 (1H, d, J 8.8 Hz),7.49 (2H, d, J 7.9 Hz), 2.45 (3H, s)

2-(4-Chlorophenyl)-6-nitrobenzo[d]oxazole

LCMS RT=7.76 min; ¹H NMR (DMSO): 8.77 (1H, d, J 2.2 Hz), 8.35 (1H, dd, J8.7 2.2 Hz), 8.27 (2H, d, J 8.2 Hz), 8.06 (1H, d, J 8.8 Hz), 7.76 (2H,d, J 7.9 Hz)

2-p-Tolyloxazolo[4,5-c]pyridine

LCMS RT=6.24 min, MH⁺ 211.0; ¹H NMR (DMSO): 9.11 (1H, d, J 0.9 Hz), 8.59(1H, d, J 5.6 Hz), 8.14 (2H, d, J 8.2 Hz), 7.90 (1H, dd, J 5.6 1.0 Hz),7.47 (2H, d, J 8.0 Hz), 2.44 (3H, s)

2-m-Tolylbenzo[d]oxazol-5-amine

LCMS RT=6.18 min, MH⁺ 225.0; ¹H NMR (DMSO): 7.97-7.91 (2H, m), 7.50-7.39(3H, m), 6.87 (1H, d, J 2.0 Hz), 6.67 (1H, dd, J 8.7 2.2 Hz), 5.11 (2H,s), 2.42 (3H, s)

2-(3-(Dimethylamino)phenyl)benzo[d]oxazol-5-amine

LCMS RT=6.12 min, MH⁺ 254.0; ¹H NMR (DMSO): 7.48-7.31 (4H, m), 6.96-6.92(1H, m), 6.87 (1H, d, J 2.2 Hz), 6.66 (1H, dd, J 8.6 2.2 Hz), 5.09 (2H,s), 3.00 (6H, s)

5-Bromo-2-p-tolylbenzo[d]oxazole

LCMS RT=9.41 min, MH⁺ 289.8; ¹H NMR (DMSO): 8.10 (2H, d, J 8.2 Hz), 8.04(1H, d, J 1.9 Hz), 7.78 (1H, d, J 8.6 Hz), 7.58 (1H, dd, J 8.7 2.0 Hz),7.45 (2H, d, J 8.0 Hz), 2.43 (3H, s)

2-o-Tolylbenzo[d]oxazol-5-amine

LCMS RT=6.16 min, MH⁺ 225.0; ¹H NMR (DMSO): 8.05 (1H, d, J 7.7 Hz),7.53-7.37 (4H, m), 6.90 (1H, d, J 2.2 Hz), 6.68 (1H, dd, J 8.7 2.2 Hz),5.10 (2H, s), 2.71 (3H, s)

2-(2-Chlorophenyl)benzo[d]oxazol-5-amine

LCMS RT=4.31 min, MH⁺ 245.0; ¹H NMR (DMSO): 8.10 (1H, d, J 7.3 Hz),7.75-7.52 (3H, m), 7.45 (1H, d, J 8.6 Hz), 6.92 (1H, d, J 1.6 Hz), 6.73(1H, dd, J 8.8 2.1 Hz), 5.16 (2H, s)

6-Bromo-2-p-tolyloxazolo[5,4-b]pyridine

LCMS RT=8.40 min, MH⁺ 288.8; ¹H NMR (DMSO): 8.59 (1H, d, J 2.1 Hz), 8.50(1H, d, J 2.2 Hz), 8.13 (2H, d, J 8.2 Hz), 7.48 (2H, d, J 8.0 Hz)

5,6-Dimethyl-2-p-tolylbenzo[d]oxazole

LCMS RT=8.76 min, MH⁺ 238.0; ¹H NMR (DMSO): 8.06 (2H, d, J 8.2 Hz), 7.56(2H, s), 7.41 (2H, d, J 8.2 Hz), 2.41 (3H, s), 2.35 (3H, s), 2.33 (3H,s)

2-(4-Chlorophenyl)-5,6-dimethylbenzo[d]oxazole

LCMS RT=9.07 min, MH⁺ 258.0; ¹H NMR (DMSO): 8.19 (2H, d, J 8.6 Hz), 7.69(2H, d, J 8.6 Hz), 7.60 (2H, s), 2.38 (3H, s), 2.36 (3H, s)

2-(2,4-Dichlorophenyl)-5,6-dimethylbenzo[d]oxazole

LCMS RT=9.68 min, MH⁺ 291.9; ¹H NMR (DMSO): 8.16 (1H, d, J 8.5 Hz), 7.90(1H, d, J 2.1 Hz), 7.69-7.61 (3H, m), 2.38 (3H, s), 2.36 (3H, s)

2-(3-Fluorophenyl)benzo[d]oxazol-5-amine

LCMS RT=9.45 min, MH⁺ 229.1; ¹H NMR (DMSO): 7.98 (1H, d, J 8.0 Hz),7.89-7.84 (1H, m), 7.68-7.60 (1H, m), 7.48-7.42 (2H, m), 6.89 (1H, d, J2.1 Hz), 6.71 (1H, dd, J 8.7 2.2 Hz), 5.15 (2H, s)

2-(5-Butylpyridin-2-yl)-6-nitrobenzo[d]oxazole

LCMS RT=7.34 min, MH⁺ 298.0; ¹H NMR (DMSO): 8.81 (1H, d, J 2.1 Hz), 8.71(1H, d, J 1.5 Hz), 8.37-8.32 (2H, m), 8.08 (1H, d, J 8.8 Hz), 7.95 (1H,dd, J 8.1 2.1 Hz), 2.75 (2H, t, J 7.6 Hz), 1.70-1.59 (2H, m), 1.41-1.29(2H, m), 0.93 (3H, t, J 7.3 Hz)

2-(4-Chlorophenyl)-5-(isopropylsulfonyl)benzo[d]oxazole

LCMS RT=6.98 min; ¹H NMR (DMSO): 8.29-8.24 (3H, m), 8.09 (1H, d, J 8.6Hz), 7.94 (1H, dd, J 8.6 1.7 Hz), 7.74 (2H, d, J 8.6 Hz), 3.56-3.50 (1H,m), 1.19 (6H, d, J 6.8 Hz)

5-Bromo-2-(4-chlorophenyl)benzo[d]oxazole

LCMS RT=9.09 min, MH⁺ 307.9; ¹H NMR (DMSO): 8.21 (2H, d, J 8.7 Hz), 8.08(1H, d, J 1.9 Hz), 7.80 (1H, d, J 8.7 Hz), 7.71 (2H, d, J 8.7 Hz), 7.62(1H, dd, J 8.7 2.0 Hz)

4-(5-Chlorobenzo[d]oxazol-2-yl)aniline

LCMS RT=6.48 min, MH⁺ 244.9; ¹H NMR (DMSO): 7.86 (2H, d, J 8.5 Hz), 7.74(1H, d, J 2.1 Hz), 7.70 (1H, d, J 8.6 Hz), 7.34 (1H, dd, J 8.8 2.1 Hz),6.70 (2H, d, J 8.7 Hz), 6.06 (2H, s)

4-(6-Chlorobenzo[d]oxazol-2-yl)aniline

LCMS RT=6.57 min, MH⁺ 245.0; ¹H NMR (DMSO): 7.87-7.82 (3H, m), 7.66 (1H,d, J 8.5 Hz), 7.37 (1H, dd, J 8.7 2.0 Hz), 6.70 (2H, d, J 8.8 Hz), 6.04(2H, s)

2-(3-Chlorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=6.78 min; ¹H NMR (DMSO): 8.34 (1H, d, J 1.3 Hz), 8.23-8.20 (2H,m), 8.10 (1H, d, J 8.6 Hz), 7.99 (1H, dd, J 8.6 1.8 Hz), 7.80-7.76 (1H,m), 7.72-7.67 (1H, m), 3.40 (2H, q, J 7.3 Hz), 1.13 (3H, t, J 7.3 Hz)

2-(2-Chlorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=6.37 min; ¹H NMR (DMSO): 8.39 (1H, d, J 1.6 Hz), 8.20 (1H, dd, J7.6 1.7 Hz), 8.12 (1H, d, J 8.6 Hz), 8.01 (1H, dd, J 8.6 1.8 Hz),7.78-7.60 (3H, m), 1.14 (3H, t, J=7.3 Hz)

2-(3,4-Dichlorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=7.25 min; ¹H NMR (DMSO): 8.39 (1H, d, J 2.0 Hz), 8.35 (1H, d, J1.4 Hz), 8.19 (1H, dd, J 8.4 2.0 Hz), 8.10 (1H, d, J 8.6 Hz), 7.99 (1H,dd, J 8.6 1.8 Hz), 7.94 (1H, d, J 8.4 Hz), 3.41 (2H, q, J 7.3 Hz), 1.13(3H, t, J 7.3 Hz)

2-(2,3-Dichlorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=6.80 min; ¹H NMR (DMSO): 8.42 (1H, d, J 1.8 0.6 Hz), 8.17-8.13(2H, m), 8.05-7.96 (2H, m), 7.65 (1H, t, J 8.0 Hz), 3.41 (2H, q, J 7.3Hz), 1.14 (3H, t, J 7.3 Hz)

2-(1-Phenylethyl)benzo[d]oxazol-5-amine

LCMS RT=5.80 min, MH⁺ 239.0; ¹H NMR (DMSO): 7.35-7.23 (6H, m), 6.80 (1H,d, J 2.1 Hz), 6.57 (1H, dd, J 8.6 2.2 Hz), 5.02 (2H, s), 4.42 (1H, q, J7.1 Hz), 1.66 (3H, d, J 7.2 Hz)

2-(4-Chlorophenyl)benzo[d]oxazole-5-sulfonic acid

LCMS RT=4.44 min, MH⁺ 309.9; ¹H NMR (DMSO): 8.28 (2H, d, J 8.7 Hz), 8.03(1H, s), 7.83-7.73 (4H, m)

5-Chloro-2-(pyridin-4-yl)benzo[d]oxazole

LCMS RT=6.51 min, MH⁺ 231.0; ¹H NMR (DMSO): 8.87 (2H, d, J 8.6 Hz), 8.11(2H, d, J 6.1 Hz), 8.04 (1H, d, J 1.8 Hz), 7.92 (1H, d, J 8.8 Hz), 7.57(1H, dd, J 8.7 2.1 Hz)

6-Chloro-2-(pyridin-4-yl)benzo[d]oxazole

LCMS RT=6.49 min, MH⁺ 231.0; ¹H NMR (DMSO): 8.87 (2H, d, J 6.1 Hz),8.10-8.08 (3H, m), 7.93 (1H, d, J 8.6 Hz), 7.54 (1H, dd, J 8.6 2.0 Hz)

4-(5-Bromobenzo[d]oxazol-2-yl)aniline

LCMS RT=6.70 min, MH⁺ 289.2; ¹H NMR (DMSO): 7.88-7.83 (3H, m), 7.66 (1H,d, J 8.6 Hz), 7.46 (1H, dd, J 8.6 2.1 Hz), 6.69 (2H, d, J 8.8 Hz), 6.09(2H, s)

2-(4-Chlorophenyl)-5-(methylsulfonyl)benzo[d]oxazole

LCMS RT=6.43 min, MH⁺ 308.2; ¹H NMR (CDCl₃): 8.43 (1H, dd, J 1.8 0.3Hz), 8.28 (2H, d, J 8.7 Hz), 8.05 (1H, dd, J 8.6 1.9 Hz), 7.81 (1H, dd,J 8.5 0.4 Hz), 7.61 (2H, d, J 8.8 Hz), 3.18 (3H, s)

2-(4-Chlorophenyl)-5-(propylsulfonyl)benzo[d]oxazole

LCMS RT=7.09 min, MH⁺ 335.9; ¹H NMR (CDCl₃): 8.38 (1H, dd, J 1.7 0.4Hz), 8.27 (2H, d, J 8.8 Hz), 8.00 (1H, dd, J 8.5 1.8 Hz), 7.80 (1H, dd,J 8.5 0.4 Hz), 7.60 (2H, d, J 8.8 Hz), 3.21-3.15 (2H, m), 1.89-1.76 (2H,m), 1.05 (3H, t, J 7.4 Hz)

2-(Naphthalen-1-yl)benzo[d]oxazol-5-amine

LCMS RT=6.59 min, MH⁺ 261.1; ¹H NMR (DMSO): 9.41 (1H, d, J 8.6 Hz), 8.38(1H, dd, J 7.3 1.0 Hz), 8.19 (1H, d, J 8.2 Hz), 8.09 (1H, dd, J 7.8 0.9Hz), 7.79-7.64 (3H, m), 7.49 (1H, d, J 8.7 Hz), 6.99 (1H, d, J 2.1 Hz),6.74 (1H, d, J 8.7 2.2 Hz), 5.17 (2H, s)

2-(Biphenyl-4-yl)benzo[d]oxazol-5-amine

LCMS RT=6.92 min, MH⁺ 287.1; ¹H NMR (DMSO): 8.22 (2H, d, J 8.2 Hz), 7.90(2H, d, J 8.3 Hz), 7.81-7.76 (2H, m), 7.53 (2H, t, J 7.8 Hz), 7.47-7.41(2H, m), 6.90 (1H, d, J 2.2 Hz), 6.69 (1H, d, J 8.6 2.2 Hz), 5.14 (2H,s)

2-(Quinolin-2-yl)benzo[d]oxazol-5-amine

LCMS RT=5.78 min, MH⁺ 262.1; ¹H NMR (DMSO): 8.60 (1H, d, J 8.7 Hz), 8.39(1H, d, J 8.6 Hz), 8.19 (1H, dd, J 8.3 0.5 Hz), 8.10 (1H, dd, J 8.4 0.8Hz), 7.92-7.86 (1H, m), 7.76-7.70 (1H, m), 7.56 (1H, d, J 8.7 Hz), 6.97(1H, d, J 2.1 Hz), 6.79 (1H, dd, J 8.7 2.2 Hz), 5.22 (2H, s)

2-(Quinolin-3-yl)benzo[d]oxazol-5-amine

LCMS RT=5.76 min, MH⁺ 262.1; ¹H NMR (DMSO): 9.58 (1H, d, J 2.1 Hz), 8.14(1H, d, J 2.0 Hz), 8.24 (1H, dd, J 7.8 0.8 Hz), 8.13 (1H, d, J 8.3 Hz),7.93-7.88 (1H, m), 7.74 (1H, td, J 8.0 0.9 Hz), 7.49 (1H, d, J 8.6 Hz),6.95 (1H, d, J 2.1 Hz), 6.74 (1H, dd, J 8.7 2.2 Hz), 5.20 (2H, s)

2-(6-Methoxynaphthalen-2-yl)benzo[d]oxazol-5-amine

LCMS RT=6.56 min, MH⁺ 291.1; ¹H NMR (DMSO): 8.67 (1H, d, J 1.3 Hz), 8.16(1H, dd, J 8.6 1.7 Hz), 8.07 (1H, d, J 9.1 Hz), 7.99 (1H, d, J 8.8 Hz),7.45-7.42 (2H, m), 7.27 (1H, dd, J 8.7 2.5 Hz), 6.90 (1H, d, J 2.0 Hz),6.68 (1H, dd, J 8.6 2.2 Hz), 5.12 (2H, s), 3.92 (3H, s)

2-(6-Bromonaphthalen-2-yl)benzo[d]oxazol-5-amine

LCMS RT=7.59 min, MH⁺ 339.3; ¹H NMR (DMSO): 8.78 (1H, s), 8.34 (1H, d, J1.7 Hz), 8.26 (1H, d, J 8.6 1.6 Hz), 8.14 (1H, d, J 8.9 Hz), 8.09 (1H,d, J 8.7 Hz), 7.76 (1H, dd, J 8.9 2.0 Hz), 7.46 (1H, d, J 8.7 Hz), 6.92(1H, d, J 2.2 Hz), 6.72 (1H, dd, J 8.6 2.2 Hz), 5.16 (2H, s)

2-(4-Chlorophenyl)naphtho[1,2-d]oxazole

LCMS RT=9.55 min, MH⁺ 280.1; ¹H NMR (DMSO): 8.47 (1H, dd, J 8.2 0.6 Hz),8.29 (2H, d, J 8.7 Hz), 8.17-8.13 (1H, m), 8.02 (2H, s), 7.78-7.70 (3H,m), 7.67-7.61 (1H, m)

1-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)propan-1-one

LCMS RT=7.92 min, MH⁺ 286.1; ¹H NMR (DMSO): 8.44 (1H, dd, J 1.7 0.4 Hz),8.24 (2H, d, J 8.7 Hz), 8.09 (1H, dd, J 8.6 1.7 Hz), 7.93 (1H, dd, J 8.60.4 Hz), 7.73 (2H, d, J 8.8 Hz), 3.17 (2H, q, J 7.2 Hz), 1.13 (3H, t, J7.1 Hz)

1-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)ethanone

LCMS RT=7.27 min, MH⁺ 271.7; ¹H NMR (DMSO): 8.44 (1H, dd, J 1.7 0.4 Hz),8.24 (2H, d, J 8.8 Hz), 8.08 (1H, dd, J 8.6 1.7 Hz), 7.93 (1H, dd, J 8.50.5 Hz), 7.73 (2H, d, J 8.8 Hz), 2.69 (3H, s)

2-(4-Cyclohexylphenyl)benzo[d]oxazol-5-amine

LCMS RT=8.15 min, MH⁺ 293.1; ¹H NMR (DMSO): 8.05 (2H, d, J 8.4 Hz),7.45-7.38 (3H, m), 6.86 (1H, d, J 2.0 Hz), 6.65 (1H, dd, J 8.8 2.2 Hz),5.10 (2H, s), 2.64-2.56 (1H, m), 1.83-1.70 (5H, m), 1.51-1.23 (5H, m)

5-(Ethylsulfonyl)-2-(quinolin-2-yl)benzo[d]oxazole

LCMS RT=6.14 min, MH⁺ 339.1; ¹H NMR (DMSO): 8.69 (1H, dd, J 8.5 2.2 Hz),8.52-8.43 (2H, m), 8.28-8.21 (2H, m), 8.16 (1H, d, J 8.1 Hz), 8.09-8.04(1H, m), 7.97-7.90 (1H, m), 7.82-7.76 (1H, m), 3.48-3.38 (2H, m), 1.15(3H, td, J 7.3 1.3 Hz)

5-(Ethylsulfonyl)-2-(quinolin-3-yl)benzo[d]oxazole

LCMS RT=6.05 min, MH⁺ 339.1; ¹H NMR (DMSO): 9.65 (1H, d, J 2.1 Hz), 9.31(1H, d, J 2.1 Hz), 8.40 (1H, d, J 1.8 Hz), 8.31 (1H, d, J 8.1 Hz), 8.17(2H, dd, J 8.3 2.2 Hz), 8.02 (1H, dd, J 8.7 1.8 Hz), 8.00-7.93 (1H, m),7.82-7.76 (1H, m), 3.43 (2H, q, J 7.3 Hz), 1.15 (3H, t, J 7.5 Hz)

2-(6-Bromonaphthalen-2-yl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=7.86 min, MH⁺ 418.0; ¹H NMR (DMSO): 8.95 (1H, m), 8.39-8.33 (3H,m), 8.21 (1H, d, J 9.0 Hz), 8.17 (1H, d, J 8.9 Hz), 8.13 (1H, dd, J 8.50.5 Hz), 7.99 (1H, dd, J 8.6 1.8 Hz), 7.81 (1H, dd, J 8.7 1.9 Hz), 3.41(2H, q, J 7.3 Hz), 1.15 (3H, t, J 7.5 Hz)

2-(4-Cyclohexylphenyl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=8.56 min; ¹H NMR (DMSO): 8.29 (1H, dd, J 1.8 0.4 Hz), 8.17 (2H,d, J 8.3 Hz), 8.07 (1H, dd, J 8.6 0.5 Hz), 7.94 (1H, dd, J 8.5 1.8 Hz),7.51 (2H, d, J 8.4 Hz), 3.39 (2H, q, J 7.3 Hz), 2.74-2.60 (1H, m),1.84-1.71 (5H, m), 1.53-1.24 (5H, m), 1.13 (3H, t, J 7.5 Hz)

2-(Biphenyl-4-yl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=7.31 min, MH⁺ 364.1; ¹H NMR (DMSO): 8.36-8.32 (3H, m), 8.11 (1H,dd, J 8.6 0.5 Hz), 8.00-7.95 (3H, m), 7.84-7.79 (2H, m), 7.57-7.43 (3H,m), 3.41 (2H, q, J 7.3 Hz), 1.14 (3H, t, J 7.5 Hz)

5-(Ethylsulfonyl)-2-(naphthalen-1-yl)benzo[d]oxazole

LCMS RT=7.03 min, MH⁺ 338.1; ¹H NMR (DMSO): 9.41 (1H, d, J 8.8 Hz), 8.52(1H, dd, J 7.2 1.2 Hz), 8.44 (1H, d, J 1.7 Hz), 8.30 (1H, d, J 8.3 Hz),8.17-8.12 (2H, m), 8.02 (1H, dd, J 8.6 1.8 Hz), 7.84-7.68 (3H, m), 3.43(2H, q, J 7.3 Hz), 1.15 (3H, t, J 7.5 Hz)

5-(Ethylsulfonyl)-2-(6-fluoronaphthalen-2-yl)benzo[d]oxazole

LCMS RT=7.29 min, MH⁺ 356.1; ¹H NMR (DMSO): 8.97 (1H, m), 8.37-8.32 (3H,m), 8.17 (1H, d, J 8.9 Hz), 8.12 (1H, d, J 8.6 Hz), 7.99 (1H, dd, J 8.61.6 Hz), 7.89 (1H, dd, J 10.0 2.0 Hz), 7.61 (1H, td, J 8.7 2.0 Hz), 3.41(2H, q, J 7.3 Hz), 1.14 (3H, t, J 7.5 Hz)

2-(Benzo[b]thiophen-5-yl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=6.77 min, MH⁺ 344.1; ¹H NMR (CDCl₃): 8.70 (1H, d, J 1.2 Hz),8.27 (1H, dd, J 1.8 0.4 Hz), 8.18 (1H, dd, J 8.5 1.5 Hz), 7.99 (1H, d, J8.6 Hz), 7.88 (1H, dd, J 8.5 1.8 Hz), 7.70 (1H, dd, J 8.5 0.4 Hz), 7.52(1H, d, J 5.5 Hz), 7.43 (1H, dd, J 5.5 0.6 Hz), 3.12 (2H, q, J 7.4 Hz),1.25 (3H, t, J 7.4 Hz)

5-Amino-2-(5,6-dichlorobenzo[d]oxazol-2-yl)phenol

LCMS RT=7.83 min, MH⁺ 295.1; ¹H NMR (DMSO): 10.88 (1H, s), 8.19 (1H, s),8.06 (1H, s), 7.69 (1H, d, J 8.7 Hz), 6.35 (1H, dd, J 8.7 2.1 Hz), 6.29(2H, br), 6.24 (1H, d, J 2.1 Hz)

2-(3,4-Dichlorophenyl)-5-(isopropylsulfonyl)benzo[d]oxazole

LCMS RT=7.68 min; ¹H NMR (DMSO): 8.41 (1H, d, J 2.0 Hz), 8.31 (1H, dd, J1.8 0.4 Hz), 8.21 (1H, dd, J 8.4 2.0 Hz), 8.11 (1H, dd, J 8.6 0.5 Hz),7.98-7.93 (2H, m), 3.59-3.50 (1H, m), 1.19 (6H, d, J 6.8 Hz)

N-(4-(5,6-Dimethylbenzo[d]oxazol-2-yl)-3-hydroxyphenyl)acetamide

LCMS RT=6.70 min, MH⁺ 263.1; ¹H NMR (DMSO): 10.83 (1H, s), 8.02 (1H, dd,J 9.9 6.9 Hz), 7.85 (1H, dd, J 10.4 7.5 Hz), 7.62 (1H, d, J 8.6 Hz),6.29 (1H, dd, J 8.7 2.1 Hz), 6.18 (1H, d, J 2.0 Hz), 6.15 (2H, br)

4-(5,6-Dichlorobenzo[d]oxazol-2-yl)aniline

LCMS RT=7.27 min, MH⁺ 279.0; ¹H NMR (DMSO): 8.10 (1H, s), 7.97 (1H, s),7.85 (2H, d, J 8.7 Hz), 6.70 (2H, d, J 8.8 Hz), 6.14 (2H, s)

5-(Ethylsulfonyl)-2-(5,6,7,8-tetrahydronaphthalen-2-yl)benzo[d]oxazole

LCMS RT=7.71 min, MH⁺ 342.2; ¹H NMR (CDCl₃): 8.03 (1H, dd, J 1.8 0.5Hz), 7.93-7.87 (2H, m), 7.85 (1H, dd, J 8.5 1.8 Hz), 7.65 (1H, dd, J 8.50.5 Hz), 7.23-7.15 (1H, m), 3.11 (2H, q, J 7.4 Hz), 2.85-2.76 (4H, m),1.81-1.76 (4H, m), 1.24 (3H, t, J 7.3 Hz)

5-Amino-2-(5-(ethylsulfonyl)benzo[d]oxazol-2-yl)phenol

LCMS RT=5.99 min, MH⁺ 319.2; ¹H NMR (DMSO): 10.88 (1H, s), 8.16 (1H, dd,J 1.8 0.5 Hz), 7.97 (1H, dd, J 8.5 0.5 Hz), 7.84 (1H, dd, J 8.4 1.9 Hz),7.69 (1H, d, J 8.6 Hz), 6.31 (1H, dd, J 8.7 2.1 Hz), 6.24 (2H, s), 6.20(1H, d, J 2.1 Hz), 3.37 (2H, q, J 7.5 Hz), 1.12 (3H, t, J 7.3 Hz)

Method 1A (Compounds Ic)N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)nicotinamide

LCMS RT=4.64 min, MH⁺ 317.1; ¹H NMR (DMSO): 10.67 (1H, s), 9.37 (1H, d,J 1.5 Hz), 9.16 (1H, d, J 1.6 Hz), 8.84-8.78 (2H, m), 8.56 (1H, dt, J8.0 1.7 Hz), 8.36-8.32 (2H, m), 7.86 (1H, d, J 8.8 Hz), 7.80 (1H, dd, J8.9 2.0 Hz), 7.70-7.58 (2H, m)

4-Methoxy-N-(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)benzamide

¹H NMR (DMSO): 10.25 (1H, s), 8.23 (1H, s), 8.16 (2H, d, J 8.9 Hz), 8.00(2H, d, J 8.9 Hz), 7.72 (2H, s), 7.17 (2H, d, J 9.0 Hz), 7.09 (2H, d, J8.8 Hz), 3.88 (3H, s), 3.85 (3H, s)

N-(2-benzylbenzo[d]oxazol-5-yl)-2-phenylacetamide

LCMS RT=6.22 min, MH⁺ 343.1; ¹H NMR (CDCl₃): 7.70 (1H, s), 7.42 (1H, s),7.30-7.15 (12H, m), 4.14 (2H, s), 3.63 (2H, s)

2,3-Dichloro-N-(2-(2,3-dichlorophenyl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=8.09 min, MH⁺ 450.9; ¹H NMR (DMSO): 10.84 (1H, s), 8.32 (1H, d,J 1.7 Hz), 8.14 (1H, dd, J 8.9 1.5 Hz), 7.95 (1H, dd, J 8.1 1.6 Hz),7.85 (1H, d, J 8.8 Hz), 7.81 (1H, dd, J 8.0 1.6 Hz), 7.73 (1H, dd, J 8.82.1 Hz), 7.65-7.50 (3H, m)

Method 1A (Compounds Id)2′-(4-Propylphenyl)-2,6′-bibenzo[d]oxazole-6-carboxylic acid

¹H NMR (DMSO): 13.20 (1H, br), 8.58 (1H, dd, J 1.5 0.4 Hz), 8.33-8.30(2H, m), 8.19 (2H, d, J 8.2 Hz), 8.06-0.802 (2H, m), 7.93 (1H, d, J 8.3Hz), 7.50 (2H, d, J 8.4 Hz), 2.69 (2H, t, J 7.8 Hz), 1.73-1.61 (2H, m),0.94 (3H, t, J 7.4 Hz)

Method 1A (Compounds Ie)4-Amino-N-(4-(5-bromobenzo[d]oxazol-2-yl)phenyl)benzamide

LCMS RT=6.87 min, MH⁺ 408.0; ¹H NMR (DMSO): 10.14 (1H, s), 8.16 (2H, d,J 8.9 Hz), 8.07-8.01 (3H, m), 7.79-7.74 (3H, m), 7.57 (1H, dd, J 8.6 2.0Hz), 6.62 (2H, d, J 8.7 Hz), 5.86 (2H, s)

Method 1B (Compounds I) 2-Benzyl-5-nitrobenzo[d]oxazole

To 2-amino-4-nitrophenol (300 mg, 1.95 mmol) in dioxane (2.5 mL) wasadded 2-phenylacetyl chloride (290 μL, 2.15 mmol) at room temperature.The reaction vessel was heated in the microwave at 210° C. for 15 min.After cooling, the mixture was slowly poured into 1M aqueous sodiumhydroxide (50 mL), and the resulting precipitate filtered and washedwith water. The resulting solid was purified by column chromatographyeluting using a gradient (ethyl acetate/hexanes 1:7 v/v to ethylacetate/hexanes 1:5 v/v) to afford 165 mg (33%) of the title compound(LCMS RT=6.47 min, MH⁺ 255.2)

¹H NMR (DMSO): 8.60 (1H, d, J 2.4 Hz), 8.30 (1H, dd, J 9.0 2.4 Hz), 7.95(1H, d, J 9.0 Hz), 7.43-7.27 (5H, m), 4.44 (2H, s)

All compounds below were prepared following the same general method. Theacid chloride used was either a commercially available compound orsynthesized from the corresponding carboxylic acid using standardconditions.

2-(Benzo[d][1,3]dioxol-5-yl)-5-nitrobenzo[d]oxazole

LCMS RT=6.74 min, MH⁺ 284.9; ¹H NMR (DMSO): 8.60 (1H, d, J 2.3 Hz), 8.31(1H, dd, J 8.9 2.3 Hz), 7.99 (1H, d, J 9.0 Hz), 7.82 (1H, dd, J 8.2 1.7Hz), 7.66 (1H, d, J 1.6 Hz), 7.18 (1H, d, J 8.4 Hz), 6.20 (2H, s)

2-(4-Chlorophenyl)-5,6-methylenedioxybenzoxazole

LCMS RT=7.54 min, MH⁺ 274.0; ¹H NMR (DMSO): 8.11 (2H, d, J 8.8 Hz), 7.66(2H, d, J 8.7 Hz), 7.49 (1H, s), 7.36 (1H, s), 6.13 (2H, s)

5-Tert-butyl-2-(4-chlorophenyl)benzo[d]oxazole

LCMS RT=10.20 min, MH⁺ 286.0; ¹H NMR (DMSO): 8.20 (2H, d, J 8.6 Hz),7.80 (1H, d, J 1.9 Hz), 7.72-7.68 (3H, m), 7.52 (1H, dd, J 8.7 2.0 Hz),1.37 (9H, s)

2-(3,4-Dichlorophenyl)-6-nitrobenzo[d]oxazole

LCMS RT=8.40 min; ¹H NMR (DMSO): 8.77 (1H, d, J 2.1 Hz), 8.40 (1H, d, J2.0 Hz), 8.36 (1H, dd, J 8.8 2.2 Hz), 8.21 (1H, dd, J 8.5 2.1 Hz), 8.07(1H, d, J 8.8 Hz), 7.96 (1H, d, J 8.4 Hz)

2-(4-Chlorophenyl)benzo[d]oxazole-5-sulfonamide

LCMS RT=6.04 min; ¹H NMR (DMSO): 8.27-8.22 (3H, m), 8.02 (1H, d, J 8.6Hz), 7.95-7.91 (1H, m), 7.74-7.71 (2H, m), 7.50 (2H, s)

5-Chloro-2-(4-chlorophenyl)-6-nitrobenzo[d]oxazole

LCMS RT=8.10 min; ¹H NMR (DMSO): 8.73 (1H, s), 8.31 (1H, s), 8.24 (2H,d, J 8.7 Hz), 7.76 (2H, d, J 8.7 Hz)

5-Nitro-2-(4-(trifluoromethoxy)phenyl)benzo[d]oxazole

LCMS RT=7.66 min; ¹H NMR (DMSO): 8.72 (1H, d, J 2.3 Hz), 8.38 (3H, m),8.09 (1H, d, J 8.8 Hz), 7.66 (2H, d, J 8.2 Hz)

2-(3,4-Dichlorophenyl)benzo[d]oxazole[1,3]dioxole

LCMS RT=8.70 min, MH⁺ 307.9; ¹H NMR (CDCl₃): 8.18 (1H, d, J 2.0 Hz),7.91 (1H, dd, J 8.4 2.0 Hz), 7.50 (1H, d, J 8.4 Hz), 7.09 (1H, s), 6.99(1H, s), 5.99 (2H, s)

2-(Furan-2-yl)-5-nitrobenzo[d]oxazole

LCMS RT=6.24 min; ¹H NMR (DMSO): 8.66 (1H, d, J 2.3 Hz), 8.35 (1H, dd, J9.0 2.4 Hz), 8.18 (1H, d, J 1.0 Hz), 8.05 (1H, d, J 9.0 Hz), 7.62 (1H,d, J 3.5 Hz), 6.90-6.88 (1H, m)

2-(Benzo[d][1,3]dioxol-5-yl)-5-chloro-6-nitrobenzo[d]oxazole

LCMS RT=7.21 min; ¹H NMR (DMSO): 8.68 (1H, s), 8.23 (1H, s), 7.83 (1H,dd, J 8.2 1.6 Hz), 7.66 (1H, d, J 1.7 Hz), 7.20 (1H, d, J 8.4 Hz), 6.22(2H, s)

5-(Ethylsulfonyl)-2-(naphthalen-2-yl)benzo[d]oxazole

LCMS RT=6.94 min, MH⁺ 338.1; ¹H NMR (DMSO): 8.90 (1H, br), 8.34 (1H, d,J 1.4 Hz), 8.30 (1H, dd, J 8.6 1.7 Hz), 8.24-8.05 (4H, m), 7.99 (1H, dd,J 8.5 1.8 Hz), 7.73-7.64 (2H, m), 3.41 (2H, q, J 7.3 Hz), 1.15 (3H, t, J7.3 Hz)

2-(3-Chloro-2-fluorophenyl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=6.48 min, MH⁺ 338.8; ¹H NMR (DMSO): 8.40 (1H, dd, J 1.7 0.5 Hz),8.27-8.21 (1H, m), 8.14 (1H, dd, J 8.6 0.4 Hz), 8.01 (1H, dd, J 8.6 1.8Hz), 7.97-7.92 (1H, m), 7.51 (1H, td, J 8.0 1.0 Hz), 3.41 (2H, q, J 7.3Hz), 1.13 (3H, t, J 7.3 Hz)

2-Cyclohexyl-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=6.57 min, MH⁺ 293.9; ¹H NMR (DMSO): 8.20 (1H, d, J 1.5 Hz), 7.97(1H, dd, J 8.5 Hz), 7.88 (1H, dd, J 8.6 1.8 Hz), 3.35 (2H, q, J 7.4 Hz),3.13-3.04 (1H, m), 2.14-2.09 (2H, m), 1.82-1.58 (5H, m), 1.50-1.18 (3H,m), 1.10 (3H, t, J 7.4 Hz)

2-(5-Chloropyridin-2-yl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=5.92 min, MH⁺ 323.1; ¹H NMR (DMSO): 8.91 (1H, d, J 2.4 Hz),8.42-8.39 (2H, m), 8.25 (1H, dd, J 8.5 2.4 Hz), 8.16 (1H, d, J 8.6 Hz),8.03 (1H, dd, J 8.6 1.8 Hz), 3.41 (2H, q, J 7.2 Hz), 1.13 (3H, t, J 7.3Hz)

2-(Benzo[d][1,3]dioxol-5-yl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=6.09 min, MH⁺ 332.0; ¹H NMR (DMSO): 8.26 (1H, dd, J 1.8 0.5 Hz),8.03 (1H, dd, J 8.5 0.5 Hz), 7.92 (1H, dd, J 8.5 1.8 Hz), 7.83 (1H, dd,J 8.2 1.7 Hz), 7.68 (1H, d, J 1.6 Hz), 7.19 (1H, d, J 8.2 Hz), 6.20 (2H,s), 3.39 (2H, q, J 7.3 Hz), 1.12 (3H, t, J 7.3 Hz)

5-Chloro-2-(4-(methylsulfonyl)phenyl)benzo[d]oxazole

LCMS RT=6.43 min; ¹H NMR (DMSO): 8.45 (2H, d, J 8.4 Hz), 8.18 (2H, d, J8.5 Hz), 8.02 (1H, d, J 1.9 Hz), 7.92 (1H, d, J 8.7 Hz), 7.56 (1H, dd, J8.7 2.1 Hz)

2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=6.70 min; ¹H NMR (DMSO): 8.32 (1H, dd, J 1.8 0.5 Hz), 8.24 (1H,d, J 1.6 Hz), 8.16 (1H, dd, J 8.5 1.7 Hz), 8.09 (1H, dd, J 8.6 0.5 Hz),7.97 (1H, dd, J 8.5 1.8 Hz), 7.71 (1H, d, J 8.5 Hz), 3.40 (2H, q, J 7.3Hz), 1.13 (3H, t, J 7.4 Hz)

2-(4-Chlorophenyl)benzo[d]oxazol-6-ol

LCMS RT=6.42 min, MH⁺ 246.0; ¹H NMR (DMSO): 9.94 (1H, s), 8.13 (2H, d, J8.6 Hz), 7.66 (2H, d, J 8.6 Hz), 7.60 (1H, d, J 8.6 Hz), 7.10 (1H, d, J2.2 Hz), 6.87 (1H, dd, J 8.7 2.3 Hz)

2-(5-(Ethylsulfonyl)benzo[d]oxazol-2-yl)naphthalen-1-ol

LCMS RT=7.77 min, MH⁺ 353.9; ¹H NMR (DMSO): 12.24 (1H, s), 8.44-8.39(2H, m), 8.19-7.98 (4H, m), 7.77-7.63 (3H, m), 3.42 (2H, q, J 7.3 Hz),1.15 (3H, t, J 7.3 Hz)

2-(Benzofuran-5-yl)-5-(ethylsulfonyl)benzo[d]oxazole

LCMS RT=6.47 min, MH⁺ 328.2; ¹H NMR (DMSO): 8.61 (1H, d, J 1.7 Hz), 8.31(1H, d, J 1.7 Hz), 8.22 (1H, dd, J 8.5 1.7 Hz), 8.19 (1H, d, J 2.2 Hz),8.09 (1H, d, J 8.5 Hz), 7.95 (1H, dd, J 8.5 1.9 Hz), 7.88 (1H, d, J 8.7Hz), 7.19-7.17 (1H, m), 3.40 (2H, q, J 7.4 Hz), 1.15 (3H, t, J 7.3 Hz)

2-(4-Chlorophenyl)-N,N-diethylbenzo[d]oxazole-5-sulfonamide

LCMS RT=7.75 min, MH⁺ 364.9; ¹H NMR (DMSO): 8.26-8.21 (3H, m), 8.03 (1H,d, J 8.6 Hz), 7.89 (1H, dd, J 8.6 1.8 Hz), 7.74 (2H, d, J 8.6 Hz), 3.22(4H, q, J 7.2 Hz), 1.06 (6H, t, J 7.2 Hz)

2-(Naphthalen-2-yl)-5-(trifluoromethoxy)benzo[d]oxazole

LCMS RT=9.10 min, MH⁺ 330.1; ¹H NMR (DMSO): 8.88 (1H, br), 8.27 (1H, dd,J 8.5 1.7 Hz), 8.23-8.19 (1H, m), 8.16 (1H, d, J 8.7 Hz), 8.08-8.04 (1H,m), 7.97 (1H, d, J 8.9 Hz), 7.95-7.93 (1H, m), 7.73-7.64 (2H, m),7.52-7.47 (1H, m)

2-(Naphthalen-2-yl)benzo[d]oxazole-5-carboxylic acid

LCMS RT=4.83 min, MH⁺ 289.0; ¹H NMR (DMSO): 13.20 (1H, br), 8.89 (1H,br), 8.36 (1H, dd, J 1.6 0.5 Hz), 8.30 (1H, dd, J 8.6 1.8 Hz), 8.24-8.20(1H, m), 8.17 (1H, d, J 8.8 Hz), 8.10-8.04 (2H, m), 7.94 (1H, dd, J 8.50.5 Hz), 7.73-7.63 (2H, m)

2-(Naphthalen-2-yl)benzo[d]oxazole

LCMS RT=8.19 min, MH⁺ 246.1; ¹H NMR (DMSO): 8.86 (1H, br), 8.29 (1H, dd,J 8.6 1.8 Hz), 8.22-8.18 (1H, m), 8.15 (1H, d, J 8.7 Hz), 8.07-8.03 (1H,m), 7.88-7.83 (2H, m), 7.71-7.62 (2H, m), 7.51-7.42 (2H, m)

5-tert-Butyl-2-(naphthalen-2-yl)benzo[d]oxazole

LCMS RT=10.50 min, MH⁺ 302.2; ¹H NMR (CDCl₃): 8.70 (1H, s), 8.25 (1H,dd, J 8.6 1.5 Hz), 7.94-7.89 (2H, m), 7.85-7.81 (1H, m), 7.77 (1H, d, J1.6 Hz), 7.54-7.45 (3H, m), 7.37 (1H, dd, J 8.5 1.8 Hz), 1.35 (9H, s)

5,6-Difluoro-2-(naphthalen-2-yl)benzo[d]oxazole

LCMS RT=8.57 min, MH⁺ 282.1; ¹H NMR (DMSO): 8.82 (1H, br), 8.24 (1H, dd,J 8.6 1.8 Hz), 8.21-8.12 (3H, m), 8.07-8.00 (2H, m), 7.72-7.63 (2H, m)

1-(2′-(3″,4″-Dichlorophenyl)benzo[d]oxazol-5′-yl)ethanone

LCMS RT=8.19 min, MH⁺ 305.9; ¹H NMR (DMSO): 8.45 (1H, dd, J 1.7 0.5 Hz),8.38 (1H, d, J 2.0 Hz), 8.18 (1H, dd, J 8.5 2.1 Hz), 8.09 (1H, dd, J 8.61.8 Hz), 7.96-7.91 (2H, m), 2.69 (3H, s)

2-(4-Chlorophenyl)-6-methylbenzo[d]oxazole

LCMS RT=8.41 min, MH⁺ 244.1; ¹H NMR (DMSO): 8.18 (2H, d, J 8.7 Hz),7.72-7.61 (4H, m), 7.27-7.23 (1H, m), 2.48 (3H, s)

5-Methyl-2-(naphthalen-2-yl)benzo[d]oxazole

LCMS RT=8.82 min, MH⁺ 260.2; ¹H NMR (DMSO): 8.83 (1H, d, J 1.1 Hz), 8.26(1H, dd, J 8.6 1.7 Hz), 8.21-8.16 (1H, m), 8.13 (1H, d, J 8.7 Hz),8.06-8.02 (1H, m), 7.72-7.64 (4H, m), 7.30-7.26 (1H, m), 2.47 (3H, s)

Method 1C (Compounds I) 6-Nitro-2-phenyloxazolo[5,4-b]pyridine

To polyphosphoric acid at 165° C. was addedN-(5-nitro-2-oxo-1,2-dihydropyridin-3-yl)benzamide (300 mg, 1.16 mmol).The resulting mixture was then heated to 165° C. for 30 min. Thesolution was then poured into water. The resulting precipitate wascollected by filtration, dissolved in diethyl ether, filtered throughalumina and evaporated to afford 9 mg (3%) of the title compound.

¹H NMR (DMSO): 9.31 (1H, d, J 2.5 Hz), 9.12 (1H, d, J 2.5 Hz), 8.32-8.27(2H, m), 7.79-7.67 (3H, m)

All compounds below were prepared following the same general method.

5-Nitro-2-(pyridin-2-yl)benzo[d]oxazole

LCMS RT=5.83 min, MH⁺ 241.9; ¹H NMR (DMSO): 8.87-8.84 (1H, m), 8.78 (1H,d, J=2.3 Hz), 8.44-8.40 (2H, m), 8.16-8.10 (2H, m), 7.74-7.69 (1H, m)

6-Nitro-2-(pyridin-2-yl)benzo[d]oxazole

LCMS RT=5.84 min, MH⁺ 242.0; ¹H NMR (DMSO): 8.79-8.76 (2H, m), 8.34 (1H,dt, J 7.9 1.0 Hz), 8.29 (1H, dd, J 8.8 2.0 Hz), 8.07-8.02 (2H, m), 7.64(1H, ddd, J 7.7 4.8 1.2 Hz)

2-(5-Butylpyridin-2-yl)-5-nitrobenzo[d]oxazole

LCMS RT=7.32 min, MH⁺ 298.1; ¹H NMR (DMSO): 8.68 (1H, dd, J 2.3 0.3 Hz),8.64 (1H, dd, J 2.1 0.5 Hz), 8.33 (1H, dd, J 9.0 2.4 Hz), 8.26 (1H, dd,J 8.0 0.6 Hz), 8.05 (1H, dd, J 9.0 0.3 Hz), 7.88 (1H, dd, J 8.1 2.1 Hz),2.70-2.66 (2H, m), 1.62-1.52 (2H, m), 1.34-1.22 (2H, m), 0.86 (3H, t, J7.4 Hz)

Method 1D (Compounds I)2-(2,4-Difluorophenyl)-5,6-dimethylbenzo[d]oxazole

A suspension of 2-(2,4-difluorobenzamido)-4,5-dimethylphenyl2,4-difluorobenzoate (90 mg, 0.22 mmol) and 4-methylbenzenesulfonic acid(82 mg, 0.43 mmol) in xylene (2 mL) was heated at reflux for 16 h. Aftercooling, the solution was diluted with ethyl acetate and washed withaqueous sodium bicarbonate solution followed by brine. The combinedorganic layers were dried over anhydrous MgSO₄ and evaporated. Theresulting solid was purified by column chromatography eluting with ethylacetate/hexanes 1:15 v/v to afford 36 mg (64%) of the title compound(LCMS RT=7.81 min, MH⁺ 260.0)

¹H NMR (DMSO): 8.30-8.22 (1H, m), 7.63-7.52 (3H, m), 7.39-7.30 (1H, m),2.37 (3H, s), 2.35 (3H, s)

Method 2A (Compounds Ib) 2-p-Tolylbenzo[d]oxazol-5-amine

To 5-nitro-2-p-tolylbenzo[d]oxazole (4.8 g, 18.90 mmol) in ethylacetate/acetic acid (250 mL/1 mL) was added palladium on carbon (480mg). The reaction vessel was purged three times with nitrogen, followedby hydrogen three times, and then left stirring under hydrogen for 16 h.The reaction vessel was finally purged three times with nitrogen, beforefiltration on a pad of Celite®, which was washed with ethyl acetate. Theorganic solution was washed with saturated aqueous Na₂CO₃, followed bybrine. The combined organic layers were dried over anhydrous MgSO₄ andevaporated to afford 2.5 g (60%) of the title compound.

¹H NMR (DMSO): 8.02 (2H, d, J 8.2 Hz), 7.39 (3H, d, J 8.5 Hz), 6.86 (1H,d, J 2.0 Hz), 6.65 (1H, dd, J 8.7 2.2 Hz), 5.09 (2H, s), 2.40 (3H, s)

Method 2B (Compounds Ib)

As Method 2A, except ethanol was used instead of ethyl acetate/aceticacid. After evaporation of the solvents, the material was taken up in 2MHCl, the resulting precipitate was discarded, and the solution wasbasified with 2N NaOH to afford the title compound as a precipitate.

2-Phenylbenzo[d]oxazol-6-amine

LCMS RT=5.93 min, MH⁺ 211.1; ¹H NMR (DMSO): 8.10-8.07 (2H, m), 7.58-7.54(3H, m), 7.42 (1H, d, J 8.4 Hz), 6.83 (1H, d, J 1.9 Hz), 6.65 (1H, dd, J8.5 2.0 Hz), 5.46 (2H, s)

Method 2C (Compounds Ib)2-(4-(Trifluoromethoxy)phenyl)benzo[d]oxazol-5-amine

To 5-nitro-2-(4-(trifluoromethoxy)phenyl)benzo[d]oxazole (850 mg, 2.62mmol) in ethanol (20 mL) was added ammonium formate (827 mg, 13.1 mmol)and palladium on carbon (85 mg). The mixture was stirred at roomtemperature for 20 min, then filtrated through a pad of Celite®, andwashed with ethyl acetate. The organic solution was washed with water,followed by brine. The combined organic layers were dried over anhydrousMgSO₄ and evaporated to afford 434 mg (56%) of the title compound (LCMSRT=6.51 min, MH⁺ 294.9)

¹H NMR (DMSO): 8.25 (2H, d, J 8.9 Hz), 7.62-7.56 (2H, m), 7.44 (1H, d, J8.7 Hz), 6.89 (1H, d, J 2.0 Hz), 6.70 (1H, dd, J 8.7 2.3 Hz), 5.16 (2H,s)

Method 2D (Compounds Ib) 2-p-Tolylbenzo[d]oxazol-4-amine

To 4-nitro-2-p-tolylbenzo[d]oxazole (330 mg, 1.30 mmol) in ethanol (20mL) was added tin (II) chloride (1.23 g, 6.5 mmol). The suspension wasstirred at 70° C. for 16 h. After cooling, the solution was poured intoice/water and neutralize with saturated aqueous NaHCO₃. The aqueouslayer was then extracted twice with ethyl acetate (500 mL). The combinedorganic layers were dried over anhydrous MgSO₄ and evaporated to afford188 mg (65%) of the title compound (LCMS RT=6.76 min, MH⁺ 225.1)

¹H NMR (DMSO): 8.04 (2H, d, J 8.2 Hz), 7.41 (2H, d, J 8.0 Hz), 7.07 (1H,t, J 8.0 Hz), 6.85 (1H, dd, J 8.0 0.8 Hz), 6.55 (1H, dd, J 8.0 0.8 Hz),5.67 (2H, s), 2.41 (3H, s)

The compound below was prepared following the same general method.

2-Phenyloxazolo[5,4-b]pyridin-6-amine

LCMS RT=5.41 min, MH⁺ 212.1; ¹H NMR (DMSO): 8.19-8.15 (2H, m), 7.73 (1H,d, J 2.4 Hz), 7.63-7.58 (3H, m), 7.32 (1H, d, J 2.4 Hz), 5.38 (2H, s)

Method 2E (Compounds Ib) 2-p-Tolylbenzo[d]oxazol-6-amine

To 6-nitro-2-p-tolylbenzo[d]oxazole (2.1 g, 8.27 mmol) in ethanol:water2:1 v/v (60 mL) at 70° C. was added iron powder (2.14 g, 38.3 mmol) andammonium chloride (819 mg, 15.3 mmol). The suspension was stirred atreflux for 16 h. After cooling, the solution was filtered through a padof Celite® and washed with ethanol. After evaporation of the solvent,the aqueous layer was extracted twice with ethyl acetate. The combinedorganic layers were dried over anhydrous MgSO₄ and evaporated. Theresulting solid was purified by column chromatography eluting with ethylacetate:hexanes 1:3 v/v to afford 70 mg (4%) of the title compound (LCMSRT=6.12 min, MH⁺ 223.1)

¹H NMR (DMSO): 7.97 (2H, d, J 8.1 Hz), 7.40-7.36 (3H, m), 6.82 (1H, d, J1.9 Hz), 6.64 (1H, dd, J 8.5 2.0 Hz), 5.41 (2H, s), 2.39 (3H, s)

All compounds below were prepared following the same general method.

2-Phenethylbenzo[d]oxazol-5-amine

LCMS RT=5.82 min, MH⁺ 238.9; ¹H NMR (DMSO): 7.29-7.16 (6H, m), 6.76 (1H,d, J 1.9 Hz), 6.57 (1H, dd, J 8.6 2.2 Hz), 4.98 (2H, s), 3.19-3.06 (4H,m)

2-(Benzo[d][1,3]dioxol-5-yl)benzo[d]oxazol-5-amine

LCMS RT=5.77 min, MH⁺ 254.9; ¹H NMR (DMSO): 7.69 (1H, dd, J 8.2 1.7 Hz),7.58 (1H, d, J 1.7 Hz), 7.37 (1H, d, J 8.6 Hz), 7.11 (1H, d, J 8.2 Hz),6.84 (1H, d, J 2.0 Hz), 6.64 (1H, dd, J 8.8 2.2 Hz), 6.16 (2H, s), 5.07(2H, s)

2-(benzo[d][1,3]dioxol-5-yl)-5-chlorobenzo[d]oxazol-6-amine

LCMS RT=6.52 min, MH⁺ 289.1; ¹H NMR (DMSO): 7.72 (1H, dd, J 8.2 1.8 Hz),7.69 (1H, s), 7.61 (1H, d, J 1.6 Hz), 7.17 (1H, d, J 8.2 Hz), 7.13 (1H,s), 6.21 (2H, s), 5.66 (2H, s)

Method 2F (Compounds Ib)

As Method 2E, except THF:water (2:1 v/v) was used instead ofethanol:water (2:1 v/v).

2-(3,4-Dichlorophenyl)benzo[d]oxazol-6-amine

LCMS RT=7.12 min, MH⁺ 278.1; ¹H NMR (DMSO): 8.22 (1H, d, J 1.8 Hz), 8.03(1H, dd, J 8.4 2.0 Hz), 7.83 (1H, d, J 8.4 Hz), 7.44 (1H, d, J 8.4 Hz),6.82 (1H, d, J 2.0 Hz), 6.68 (1H, dd, J 8.6 2.0 Hz), 5.57 (2H, s)

Method 3A (Compounds II)3-Phenyl-N-(2-phenylbenzo[d]oxazol-5-yl)propanamide

To a solution of 2-phenylbenzo[d]oxazol-5-amine (50 mg, 0.24 mmol) indichloromethane (2 mL) at room temperature was added 3-phenylpropanoylchloride (44.1 mg, 0.26 mmol) followed immediately bydiisopropylethylamine (82 μL, 0.48 mmol). The resulting mixture wasstirred at room temperature for 16 h. Dichloromethane was added and theorganic layer was washed with saturated aqueous Na₂CO₃. The combinedorganic layers were dried over anhydrous MgSO₄ and evaporated. Theresulting solid was dissolved in methanol, passed through an acidicscavenger column (silica-based quaternary amine SPE-AX from Biotage®)and then evaporated to afford 61.1 mg (75%) of the title compound (LCMSRT=6.45 min, MH⁺ 343.2)

¹H NMR (DMSO): 10.11 (1H, s), 8.22-8.15 (3H, m), 7.71 (1H, d, J 8.8 Hz),7.66-7.59 (3H, m), 7.51 (1H, dd, J 8.9 2.1 Hz), 7.33-7.17 (5H, m), 2.96(2H, t, J 7.2 Hz), 2.67 (2H, t, J 7.1 Hz)

All compounds below were prepared following the same general method.

N-(2-Phenylbenzo[d]oxazol-5-yl)acetamide

LCMS RT=5.16 min, MH⁺ 253.1; ¹H NMR (DMSO): 10.14 (1H, s), 8.21-8.14(3H, m), 7.71 (1H, d, J 8.8 Hz), 7.65-7.60 (3H, m), 7.51 (1H, dd, J 9.02.1 Hz), 2.09 (3H, s)

N-(2-Phenylbenzo[d]oxazol-5-yl)propionamide

LCMS RT=5.49 min, MH⁺ 267.1; ¹H NMR (DMSO): 10.09 (1H, s), 8.21-8.16(3H, m), 7.71 (1H, d, J 8.8 Hz), 7.66-7.61 (3H, m), 7.54 (1H, dd, J 9.02.1 Hz), 2.37 (2H, q, J 7.6 Hz), 1.12 (3H, t, J 7.6 Hz)

N-(2-Phenylbenzo[d]oxazol-5-yl)butyramide

LCMS RT=5.78 min, MH⁺ 281.1; ¹H NMR (DMSO): 10.09 (1H, s), 8.21-8.16(3H, m), 7.71 (1H, d, J 8.8 Hz), 7.64-7.60 (3H, m), 7.54 (1H, dd, J 9.02.1 Hz), 2.33 (2H, q, J 7.6 Hz), 1.69-1.61 (2H, m), 0.94 (3H, t, J 7.6Hz)

N-(2-Phenylbenzo[d]oxazol-5-yl)pentanamide

LCMS RT=6.21 min, MH⁺ 295.1; ¹H NMR (DMSO): 10.09 (1H, s), 8.21-8.16(3H, m), 7.71 (1H, d, J 8.8 Hz), 7.65-7.60 (3H, m), 7.54 (1H, dd, J 9.02.1 Hz), 2.35 (2H, q, J 7.6 Hz), 1.66-1.58 (2H, m), 1.39-1.31 (2H, m),0.92 (3H, t, J 7.6 Hz)

N-(2-Phenylbenzo[d]oxazol-5-yl)isobutyramide

LCMS RT=5.79 min, MH⁺ 281.1; ¹H NMR (DMSO): 10.02 (1H, s), 8.22-8.18(3H, m), 7.71 (1H, d, J 8.8 Hz), 7.66-7.60 (3H, m), 7.55 (1H, dd, J 9.02.1 Hz), 2.67-2.58 (1H, m), 1.14 (6H, s)

N-(2-Phenylbenzo[d]oxazol-5-yl)furan-2-carboxamide

LCMS RT=5.82 min, MH⁺ 305.1; ¹H NMR (DMSO): 10.42 (1H, s), 8.26-8.20(3H, m), 7.97 (1H, dd, J 1.7 0.8 Hz), 7.77 (2H, d, J 1.3 Hz), 7.66-7.62(3H, m), 7.38 (1H, d, J 3.4 Hz), 6.73 (1H, dd, J 3.4 1.7 Hz)

4-Chloro-N-(2-p-tolylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=7.23 min, MH⁺ 363.1; ¹H NMR (DMSO): 10.55 (1H, s), 8.32-8.31(1H, m), 8.17 (2H, d, J 8.1 Hz), 8.08 (2H, d, J 8.6 Hz), 7.84-7.77 (2H,m), 7.70 (2H, d, J 8.6 Hz), 7.50 (2H, d, J 8.1 Hz), 2.49 (3H, s)

4-Methoxy-N-(2-p-tolylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=6.41 min, MH⁺ 359.1; ¹H NMR (DMSO): 10.35 (1H, s), 8.33 (1H, s),8.17 (2H, d, J 8.1 Hz), 8.07 (2H, d, J 8.7 Hz), 7.81 (2H, s), 7.51 (2H,d, J 8.3 Hz), 7.16 (2H, d, J 8.8 Hz), 3.17 (3H, s), 2.49 (3H, s)

Method 3B (Compounds II)

As Method 3A, except instead of diisopropylamine, triethylamine was usedas a base.

N-(2-Phenylbenzo[d]oxazol-5-yl)nicotinamide

LCMS RT=5.48 min, MH⁺ 316.1; ¹H NMR (DMSO): 10.70 (1H, s), 9.21 (1H, d,J 2.1 Hz), 8.85 (1H, dd, J 4.8 1.6 Hz), 8.40 (1H, dt, J 8.0 2.0 Hz),8.37 (1H, d, J 1.8 Hz), 8.30-8.27 (2H, m), 7.89-7.80 (2H, m), 7.72-7.64(4H, m)

N-(2-Phenylbenzo[d]oxazol-5-yl)isonicotinamide

LCMS RT=5.46 min, MH⁺ 316.1; ¹H NMR (DMSO): 10.76 (1H, s), 8.88 (2H, d,J 5.9 Hz), 8.36 (1H, d, J 1.7 Hz), 8.31-8.27 (2H, m), 7.97 (2H, d, J 6.1Hz), 7.90-7.80 (2H, m), 7.73-7.68 (3H, m)

4-Chloro-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=7.07 min, MH⁺ 349.1; ¹H NMR (DMSO): 10.57 (1H, s), 8.35-8.34(1H, m), 8.30-8.27 (2H, m), 8.09 (2H, d, J 8.6 Hz), 7.88-7.80 (2H, m),7.72-7.67 (5H, m)

4-Methyl-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=6.80 min, MH⁺ 329.2; ¹H NMR (DMSO): 10.41 (1H, s), 8.37-8.35(1H, m), 8.30-8.26 (2H, m), 7.98 (2H, d, J 8.1 Hz), 7.84 (2H, s),7.72-7.67 (3H, m), 7.43 (2H, d, J 8.0 Hz), 2.47 (3H, s)

4-Methoxy-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=6.37 min, MH⁺ 345.1; ¹H NMR (DMSO): 10.33 (1H, s), 8.35 (1H, s),8.30-8.26 (2H, m), 8.06 (2H, d, J 8.7 Hz), 7.83 (2H, s), 7.71-7.67 (3H,m), 7.14 (2H, d, J 8.8 Hz), 3.92 (3H, s)

2-Methoxy-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=7.06 min, MH⁺ 345.1; ¹H NMR (DMSO): 10.37 (1H, s), 8.38-8.36(1H, m), 8.30-8.26 (2H, m), 7.84-7.56 (7H, m), 7.27 (1H, d, J 8.4 Hz),7.14 (1H, t, J 7.3 Hz), 3.99 (3H, s)

4-(Dimethylamino)-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=6.63 min, MH⁺ 358.2; ¹H NMR (DMSO): 10.10 (1H, s), 8.35-8.34(1H, m), 8.30-8.26 (2H, m), 7.96 (2H, d, J 8.9 Hz), 7.82-7.80 (2H, m),7.71-7.68 (3H, m), 6.84 (2H, d, J 8.9 Hz), 3.08 (6H, s)

3,4-Dichloro-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=7.95 min, MH⁺ 382.8; ¹H NMR (DMSO): 10.63 (1H, s), 8.37-8.26(4H, m), 8.04 (1H, dd, J 8.4 2.1 Hz), 7.92-7.78 (3H, m), 7.73-7.65 (3H,m)

N-(2-Phenylbenzo[d]oxazol-5-yl)-4-(trifluoromethyl)benzamide

LCMS RT=7.19 min, MH⁺ 383.1; ¹H NMR (DMSO): 10.72 (1H, s), 8.37-8.24(5H, m), 8.00 (2H, d, J 8.4 Hz), 7.89-7.82 (2H, m), 7.74-7.67 (3H, m)

3,5-Dichloro-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=8.30 min, MH⁺ 382.9; ¹H NMR (DMSO): 10.67 (1H, s), 8.33-8.26(3H, m), 8.09 (2H, d, J 2.1 Hz), 7.96 (1H, t, J 2.0 Hz), 7.89-7.78 (2H,m), 7.72-7.67 (3H, m)

4-Fluoro-N-(2-phenylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=6.53 min, MH⁺ 333.2; ¹H NMR (DMSO): 10.50 (1H, s), 8.34-8.33(1H, m), 8.39-8.26 (2H, m), 8.16-8.11 (2H, m), 7.86-7.79 (2H, m),7.71-7.65 (3H, m), 7.45 (2H, t, J 8.8 Hz)

N-(2-Phenylbenzo[d]oxazol-5-yl)biphenyl-4-carboxamide

LCMS RT=7.74 min, MH⁺ 391.1; ¹H NMR (DMSO): 10.55 (1H, s), 8.39-8.38(1H, m), 8.31-8.27 (2H, m), 8.17 (2H, d, J 8.5 Hz), 7.93 (2H, d, J 8.4Hz), 7.86-7.83 (4H, m), 7.72-7.69 (3H, m), 7.62-7.50 (3H, m)

2-Phenyl-N-(2-phenylbenzo[d]oxazol-5-yl)acetamide

LCMS RT=6.32 min, MH 329.2; ¹H NMR (DMSO): 10.42 (1H, s), 8.27-8.21 (3H,m), 7.78 (1H, d, J 8.9 Hz), 7.71-7.65 (3H, m), 7.61 (1H, dd, J 8.9 2.1Hz), 7.45-7.30 (5H, m), 3.75 (2H, s)

N-(2-Phenylbenzo[d]oxazol-5-yl)cinnamamide

LCMS RT=6.86 min, MH⁺ 341.1; ¹H NMR (DMSO): 10.48 (1H, s), 8.37 (1H, d,J 1.9 Hz), 8.29-8.26 (2H, m), 7.83 (1H, d, J 8.9 Hz), 7.73-7.67 (7H, m),7.56-7.48 (3H, m), 6.93 (1H, d, J 15.6 Hz)

N-(2-Phenylbenzo[d]oxazol-5-yl)-1-naphthamide

LCMS RT=7.07 min, MH⁺ 365.0; ¹H NMR (DMSO): 10.82 (1H, s), 8.44 (1H, s),8.31-8.28 (3H, m), 8.18-8.10 (2H, m), 7.88-7.83 (3H, m), 7.73-7.65 (6H,m)

N-(2-Phenylbenzo[d]oxazol-5-yl)-2-naphthamide

LCMS RT=7.37 min, MH⁺ 365.1; ¹H NMR (DMSO): 10.69 (1H, s), 8.69 (1H, s),8.42 (1H, s), 8.31-8.28 (2H, m), 8.20-8.08 (4H, m), 7.90-7.88 (2H, m),7.75-7.68 (5H, m)

N-(2-Phenylbenzo[d]oxazol-5-yl)thiophene-2-carboxamide

LCMS RT=6.31 min, MH⁺ 321.1; ¹H NMR (DMSO): 10.47 (1H, s), 8.30-8.26(3H, m), 8.12 (1H, dd, J 3.8 1.1 Hz), 7.94 (1H, dd, J 5.0 1.1 Hz), 7.85(1H, d, J 8.8 Hz), 7.77 (1H, dd, J 8.9 2.0 Hz), 7.73-7.65 (3H, m),7.33-7.30 (1H, m)

N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=5.63 min, MH⁺ 315.8; ¹H NMR (DMSO): 10.53 (1H, s), 9.45-9.42(1H, m), 8.88 (1H, dd, J 4.9 1.6 Hz), 8.62 (1H, dt, J 8.0 1.8 Hz),8.42-8.40 (1H, m), 8.06 (2H, dd, J 6.6 1.2 Hz), 7.88 (2H, s), 7.75-7.59(4H, m)

4-Chloro-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=6.12 min, MH⁺ 349.9; ¹H NMR (DMSO): 10.58 (1H, s), 9.43-9.42(1H, m), 8.89-8.87 (1H, m), 8.64-8.59 (1H, m), 8.40-8.38 (1H, m), 8.09(2H, d, J 8.5 Hz), 7.91-7.83 (2H, m), 7.76-7.69 (3H, m)

4-Methyl-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=5.91 min, MH⁺ 330.2; ¹H NMR (DMSO): 10.43 (1H, s), 9.43 (1H, dd,J 2.1 0.9 Hz), 8.88 (1H, dd, J 4.8 1.6 Hz), 8.61 (1H, dt, J 8.0 1.9 Hz),8.40 (1H, t, J 1.2 Hz), 7.98 (2H, d, J 8.2 Hz), 7.87 (2H, d, J 1.2 Hz),7.75-7.70 (1H, m), 7.43 (2H, d, J 8.0 Hz), 2.47 (3H, s)

4-Methoxy-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=5.64 min, MH⁺ 345.9; ¹H NMR (DMSO): 10.37 (1H, s), 9.45 (1H, dd,J 1.6 0.8 Hz), 8.90 (1H, dd, J 4.9 1.7 Hz), 8.63 (1H, dt, J 8.0 1.9 Hz),8.41 (1H, t, J 1.2 Hz), 8.08 (2H, d, J 8.5 Hz), 7.88 (2H, d, J 1.2 Hz),7.77-7.72 (1H, m), 7.17 (2H, d, J 8.7 Hz), 3.94 (3H, s)

2-Methoxy-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=6.02 min, MH⁺ 345.9; ¹H NMR (DMSO): 10.33 (1H, s), 9.38-9.36(1H, m), 8.82 (1H, dd, J 4.9 1.7 Hz), 8.55 (1H, dt, J 8.0 1.8 Hz),8.36-8.34 (1H, m), 7.82-7.73 (2H, m), 7.69-7.65 (2H, m), 7.57-7.50 (1H,m), 7.21 (1H, d, J 8.4 Hz), 7.09 (1H, t, J 7.6 Hz), 3.93 (3H, s)

4-(Dimethylamino)-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=5.82 min, MH⁺ 358.9; ¹H NMR (DMSO): 10.13 (1H, s), 9.45 (1H, dd,J 2.3 0.9 Hz), 8.88 (1H, dd, J 4.8 1.6 Hz), 8.64-8.59 (1H, m), 8.40-8.39(1H, m), 7.97 (2H, d, J 9.1 Hz), 7.86-7.85 (2H, m), 7.75-7.70 (1H, m),6.86 (2H, d, J 9.1 Hz), 3.08 (6H, s)

3,4-Dichloro-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=6.78 min, MH⁺ 383.5; ¹H NMR (DMSO): 10.66 (1H, s), 9.43 (1H, d,J 2.1 0.6 Hz), 8.88 (1H, dd, J 4.8 1.6 Hz), 8.61 (1H, dt, J 8.0 2.0 Hz),8.37 (1H, d, J 2.0 Hz), 8.32 (1H, d, J 2.1 Hz), 8.04 (1H, dd, J 8.4 2.1Hz), 7.92-7.82 (3H, m), 7.75-7.71 (1H, m)

N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)-4-(trifluoromethyl)benzamide

LCMS RT=6.32 min, MH⁺ 383.6; ¹H NMR (DMSO): 10.68 (1H, s), 9.37 (1H, d,J 2.1 Hz), 8.82 (1H, dd, J 4.9 1.5 Hz), 8.56 (1H, dt, J 8.0 2.0 Hz),8.34 (1H, d, J 1.7 Hz), 8.20 (2H, d, J 8.1 Hz), 7.95 (2H, d, J 8.4 Hz),7.88-7.79 (2H, m), 7.69-7.65 (1H, m)

3,5-Dichloro-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=7.06 min, MH⁺ 383.7; ¹H NMR (DMSO): 10.69 (1H, s), 9.43-9.41(1H, m), 8.88 (1H, dd, J 4.9 1.7 Hz), 8.61 (1H, dt, J 8.0 2.0 Hz), 8.37(1H, d, J 1.9 Hz), 8.09 (2H, d, J 1.9 Hz), 7.96-7.82 (3H, m), 7.75-7.71(1H, m)

4-Fluoro-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=5.70 min, MH⁺ 334.0; ¹H NMR (DMSO): 10.47 (1H, s), 9.38-9.36(1H, m), 8.82 (1H, dd, J 4.9 1.7 Hz), 8.56 (1H, dt, J 8.0 2.0 Hz),8.33-8.32 (1H, m), 8.11-8.06 (2H, m), 7.85-7.80 (2H, m), 7.69-7.65 (1H,m), 7.40 (2H, t, J 8.9 Hz)

N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)biphenyl-4-carboxamide

LCMS RT=6.78 min, MH⁺ 391.6;

2-Phenyl-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)acetamide

LCMS RT=5.63 min, MH⁺ 329.7; ¹H NMR (DMSO): 10.46 (1H, s), 9.41-9.39(1H, m), 8.87 (1H, dd, J 4.9 1.7 Hz), 8.59 (1H, dt, J 8.0 2.0 Hz), 8.26(1H, d, J 2.0 Hz), 7.82 (1H, d, J 8.8 Hz), 7.73-7.69 (1H, m), 7.64 (1H,dd, J 8.8 2.0 Hz), 7.44-7.30 (5H, m), 3.75 (2H, s)

3-Phenyl-N-(2-(pyridin-3-yl)benzo[d]oxazol-5-yl)propanamide

LCMS RT=5.84 min, MH⁺ 343.8; ¹H NMR (DMSO): 10.14 (1H, s), 9.35-9.34(1H, m), 8.81 (1H, dd, J 4.9 1.7 Hz), 8.53 (1H, dt, J 8.0 2.0 Hz), 8.19(1H, d, J 2.0 Hz), 7.76 (1H, d, J 8.8 Hz), 7.69-7.63 (1H, m), 7.54 (1H,dd, J 8.8 2.0 Hz), 7.33-7.17 (5H, m), 2.95 (2H, t, J 7.6 Hz), 2.67 (2H,t, J 8.0 Hz)

N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)cinnamamide

LCMS RT=6.03 min, MH⁺ 342.0; ¹H NMR (DMSO): 10.46 (1H, s), 9.37-9.35(1H, m), 8.82 (1H, dd, J 4.9 1.7 Hz), 8.55 (1H, dt, J 8.0 2.0 Hz), 8.35(1H, d, J 1.9 Hz), 7.82 (1H, d, J 8.9 Hz), 7.69-7.63 (5H, m), 7.49-7.41(3H, m), 6.87 (1H, d, J 15.8 Hz)

N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)propionamide

LCMS RT=4.97 min, MH⁺ 267.9; ¹H NMR (DMSO): 10.08 (1H, s), 9.34 (1H, dd,J 2.2 0.7 Hz), 8.81 (1H, dd, J 4.9 1.7 Hz), 8.53 (1H, dt, J 8.0 2.0 Hz),8.21 (1H, d, J 2.0 Hz), 7.76 (1H, d, J 8.9 Hz), 7.68-7.63 (1H, m), 7.57(1H, dd, J 9.0 2.1 Hz), 2.37 (2H, q, J 7.6 Hz), 1.12 (3H, t, J 7.6 Hz)

N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=5.26 min, MH⁺ 281.9; ¹H NMR (DMSO): 10.17 (1H, s), 9.43 (1H, dd,J 2.2 0.7 Hz), 8.89 (1H, dd, J 4.9 1.7 Hz), 8.62 (1H, dt, J 8.0 2.0 Hz),8.29 (1H, d, J 2.0 Hz), 7.84 (1H, d, J 8.9 Hz), 7.76-7.72 (1H, m), 7.65(1H, dd, J 9.0 2.1 Hz), 2.42 (2H, q, J 7.6 Hz), 1.80-1.67 (2H, m), 1.03(3H, t, J 7.6 Hz)

N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)pentanamide

LCMS RT=5.60 min, MH⁺ 296.0; ¹H NMR (DMSO): 10.09 (1H, s), 9.36-9.33(1H, m), 8.81 (1H, dd, J 4.9 1.7 Hz), 8.53 (1H, dt, J 8.0 2.0 Hz), 8.20(1H, d, J 2.0 Hz), 7.75 (1H, d, J 8.9 Hz), 7.648-7.64 (1H, m), 7.57 (1H,dd, J 9.0 2.1 Hz), 2.35 (2H, q, J 7.6 Hz), 1.66-1.56 (2H, m), 1.42-1.29(2H, m), 0.92 (3H, t, J 7.6 Hz)

N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=5.22 min, MH⁺ 282.0; ¹H NMR (DMSO): 10.11 (1H, s), 9.41 (1H, dd,J 2.2 0.7 Hz), 8.87 (1H, dd, J 4.9 1.7 Hz), 8.60 (1H, dt, J 8.0 2.0 Hz),8.29 (1H, d, J 2.0 Hz), 7.83 (1H, d, J 8.9 Hz), 7.74-7.69 (1H, m), 7.65(1H, dd, J 9.0 2.1 Hz), 2.70 (1H, t, J 6.8 Hz), 1.20 (6H, d, J 6.8 Hz)

N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)furan-2-carboxamide

LCMS RT=5.23 min, MH⁺ 305.7; ¹H NMR (DMSO): 10.41 (1H, s), 9.37 (1H, dd,J 2.2 0.8 Hz), 8.82 (1H, dd, J 4.9 1.7 Hz), 8.55 (1H, dt, J 8.0 2.0 Hz),8.30 (1H, t, J 1.3 Hz), 7.97 (1H, dd, J 1.7 0.8 Hz), 7.82-7.81 (2H, m),7.69-7.64 (1H, m), 7.37 (1H, dd, J 3.5 0.8 Hz), 6.74 (1H, dd, J 3.5 1.7Hz)

N-(2-(Pyridin-3-yl)benzo[d]oxazol-5-yl)thiophene-2-carboxamide

LCMS RT=5.55 min, MH⁺ 322.0; ¹H NMR (DMSO): 10.44 (1H, s), 9.37 (1H, dd,J 2.2 0.8 Hz), 8.82 (1H, dd, J 4.9 1.7 Hz), 8.56 (1H, dt, J 8.0 2.0 Hz),8.28 (1H, t, J 1.3 Hz), 8.06 (1H, dd, J 1.7 0.8 Hz), 7.89 (1H, dd, J 5.01.0 Hz), 7.83 (1H, d, J 9.0 Hz), 7.77-7.73 (1H, m), 7.70-7.65 (1H, m),7.26 (1H, dd, J 5.0 1.2 Hz)

N-(2-Phenylbenzo[d]oxazol-5-yl)benzamide

LCMS RT=6.82 min, MH⁺ 314.9; ¹H NMR (DMSO): 10.43 (1H, s), 8.31-8.30(1H, m), 8.25-8.20 (2H, m), 8.02-7.98 (2H, m), 7.79 (2H, d, J 1.2 Hz),7.65-7.53 (6H, m)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)nicotinamide

LCMS RT=6.55 min, MH⁺ 386.8; ¹H NMR (DMSO): 10.57 (1H, s), 9.14 (1H, d,J 2.1 Hz), 8.78 (1H, dd, J 4.8 1.6 Hz), 8.33 (1H, dt, J 8.0 2.0 Hz),8.14 (1H, d, J 1.8 Hz), 7.96 (2H, d, J 9.0 Hz), 7.70-7.52 (3H, m), 6.82(2H, d, J 9.1 Hz), 3.50-3.41 (4H, m), 1.15 (6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)isonicotinamide

LCMS RT=6.63 min, MH⁺ 386.8; ¹H NMR (DMSO): 10.69 (1H, s), 8.87 (2H, d,J 6.1 Hz), 8.20 (1H, d, J 1.5 Hz), 8.04 (2H, d, J 9.1 Hz), 7.96 (2H, d,J 6.0 Hz), 7.77-7.69 (2H, m), 6.89 (2H, d, J 9.1 Hz), 3.50-3.46 (4H, m),1.21 (6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=7.84 min, MH⁺ 386.1; ¹H NMR (DMSO): 10.43 (1H, s), 8.22-8.20(1H, m), 8.06-8.01 (4H, m), 7.72 (2H, d, J 1.2 Hz), 7.68-7.58 (3H, m),6.89 (2H, d, J 9.1 Hz), 3.51 (4H, q, J 7.0 Hz), 1.21 (6H, t, J 7.0 Hz)

4-Chloro-N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=8.60 min, MH⁺ 419.9; ¹H NMR (DMSO): 10.44 (1H, s), 8.13 (1H, s),8.00-7.95 (4H, m), 7.66-7.62 (4H, m), 6.82 (2H, d, J 9.1 Hz), 3.45 (4H,q, J 7.0 Hz), 1.15 (6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)-4-methylbenzamide

LCMS RT=8.28 min, MH⁺ 400.2; ¹H NMR (DMSO): 10.28 (1H, s), 8.14 (1H, s),7.97 (2H, d, J 8.9 Hz), 8.03 (2H, d, J 8.1 Hz), 7.65 (2H, d, J 1.2 Hz),7.36 (2H, d, J 8.1 Hz), 6.82 (2H, d, J 9.1 Hz), 3.44 (4H, q, J 7.0 Hz),2.40 (3H, s), 1.15 (6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)-4-methoxybenzamide

LCMS RT=7.86 min, MH⁺ 416.2; ¹H NMR (DMSO): 10.20 (1H, s), 8.13-8.12(1H, m), 8.00-7.95 (4H, m), 7.64 (2H, d, J 1.3 Hz), 7.07 (2H, d, J 8.9Hz), 6.82 (2H, d, J 9.1 Hz), 3.85 (3H, s), 3.44 (4H, q, J 7.0 Hz), 1.15(6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)-2-methoxybenzamide

LCMS RT=8.69 min, MH⁺ 416.0; ¹H NMR (DMSO): 10.24 (1H, s), 8.15 (1H, d,J 1.5 Hz), 7.96 (2H, d, J 8.9 Hz), 7.68-7.49 (4H, m), 7.19 (1H, d, J 8.4Hz), 7.08 (1H, t, J 7.5 Hz), 6.83 (2H, d, J 9.1 Hz), 3.92 (3H, s), 3.44(4H, q, J 7.0 Hz), 1.15 (6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)-4-(dimethylamino)benzamide

LCMS RT=8.08 min, MH⁺ 429.0; ¹H NMR (DMSO): 9.98 (1H, s), 8.13 (1H, s),7.96 (2H, d, J 8.9 Hz), 7.90 (2H, d, J 8.9 Hz), 7.64-7.61 (2H, m),6.84-6.76 (4H, m), 3.44 (4H, q, J 7.0 Hz), 3.01 (6H, s), 1.15 (6H, t, J7.0 Hz)

3,4-Dichloro-N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=9.66 min, MH⁺ 453.9; ¹H NMR (DMSO): 10.52 (1H, s), 8.25 (1H, d,J 2.0 Hz), 8.12 (1H, d, J 1.8 Hz), 7.98-7.94 (3H, m), 7.85 (1H, d, J 8.4Hz), 7.70-7.60 (2H, m), 6.82 (2H, d, J 9.2 Hz), 3.45 (4H, q, J 7.0 Hz),1.15 (6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)-4-(trifluoromethyl)benzamide

LCMS RT=8.87 min, MH⁺ 454.4; ¹H NMR (DMSO): 10.60 (1H, s), 8.20-8.15(3H, m), 7.99-7.93 (4H, m), 7.70-7.63 (2H, m), 6.83 (2H, d, J 9.2 Hz),3.45 (4H, q, J 7.0 Hz), 1.15 (6H, t, J 7.0 Hz)

3,5-Dichloro-N-(2-(4-(diethylamino)phenyl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=10.25 min, MH⁺ 453.8; ¹H NMR (DMSO): 10.63 (1H, s), 8.21-8.19(1H, m), 8.09 (2H, d, J 1.9 Hz), 8.05 (2H, d, J 9.1 Hz), 7.97 (1H, t, J1.9 Hz), 7.78-7.69 (2H, m), 6.91 (2H, d, J 9.1 Hz), 3.50 (4H, q, J 7.0Hz), 1.23 (6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)-4-fluorobenzamide

LCMS RT=7.95 min, MH⁺ 404.1; ¹H NMR (DMSO): 10.38 (1H, s), 8.13-8.12(1H, m), 8.09-8.04 (2H, m), 7.96 (2H, d, J 9.1 Hz), 7.68-7.61 (2H, m),7.39 (2H, t, J 8.9 Hz), 6.82 (2H, d, J 9.2 Hz), 3.45 (4H, q, J 7.0 Hz),1.15 (6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)biphenyl-4-carboxamide

LCMS RT=9.67 min, MH⁺ 461.9; ¹H NMR (DMSO): 10.42 (1H, s), 8.18-8.17(1H, m), 8.09 (2H, d, J 8.5 Hz), 7.98 (2H, d, J 9.0 Hz), 7.87 (2H, d, J8.6 Hz), 7.78 (2H, d, J 7.1 Hz), 7.71-7.65 (2H, m), 7.45-7.41 (3H, m),6.82 (2H, d, J 9.2 Hz), 3.45 (4H, q, J 7.0 Hz), 1.15 (6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)-2-phenylacetamide

LCMS RT=7.70 min, MH⁺ 400.1; ¹H NMR (DMSO): 10.29 (1H, s), 8.00 (1H, d,J 1.8 Hz), 7.94 (2H, d, J 9.1 Hz), 7.59 (1H, d, J 8.7 Hz), 7.45-7.23(6H, m), 6.81 (2H, d, J 9.2 Hz), 3.67 (2H, s), 3.43 (4H, q, J 7.0 Hz),1.14 (6H, t, J 7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)-3-phenylpropanamide

LCMS RT=8.10 min, MH⁺ 413.9; ¹H NMR (DMSO): 10.03 (1H, s), 7.99 (1H, d,J 1.9 Hz), 7.94 (2H, d, J 9.1 Hz), 7.58 (1H, d, J 8.7 Hz), 7.40 (1H, dd,J 8.7 2.0 Hz), 7.36-7.17 (5H, m), 6.82 (2H, d, J 9.2 Hz), 3.44 (4H, q, J7.0 Hz), 2.94 (2H, d, J 8.1 Hz), 2.65 (1H, d, J 8.3 Hz), 1.15 (6H, t, J7.0 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)propionamide

LCMS RT=6.79 min, MH⁺ 338.2; ¹H NMR (DMSO): 10.11 (1H, s), 8.07 (1H, d,J 1.9 Hz), 7.99 (2H, d, J 9.0 Hz), 7.65 (1H, d, J 8.7 Hz), 7.48 (1H, dd,J 8.8 2.0 Hz), 6.87 (2H, d, J 9.1 Hz), 3.49 (4H, q, J 7.0 Hz), 2.41 (2H,q, J 7.5 Hz), 1.24-1.14 (9H, m)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=7.24 min, MH⁺ 352.2; ¹H NMR (DMSO): 9.97 (1H, s), 8.00 (1H, d, J1.9 Hz), 7.95 (2H, d, J 9.0 Hz), 7.58 (1H, d, J 8.7 Hz), 7.43 (1H, dd, J8.8 2.0 Hz), 6.81 (2H, d, J 9.1 Hz), 3.44 (4H, q, J 7.0 Hz), 2.31 (2H,t, J 7.4 Hz), 1.68-1.58 (2H, m), 1.15 (6H, t, J 7.0 Hz), 0.94 (3H, t, J7.4 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)pentanamide

LCMS RT=7.84 min, MH⁺ 366.0; ¹H NMR (DMSO): 9.98 (1H, s), 8.00 (1H, d, J1.9 Hz), 7.95 (2H, d, J 9.0 Hz), 7.58 (1H, d, J 8.7 Hz), 7.42 (1H, dd, J8.8 2.0 Hz), 6.81 (2H, d, J 9.1 Hz), 3.44 (4H, q, J 7.0 Hz), 2.33 (2H,t, J 7.5 Hz), 1.65-1.55 (2H, m), 1.41-1.28 (2H, m), 1.15 (6H, t, J 7.0Hz), 0.91 (3H, t, J 7.4 Hz)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.25 min, MH⁺ 352.2; ¹H NMR (DMSO): 9.99 (1H, s), 8.08 (1H, d, J1.9 Hz), 8.01 (2H, d, J 9.0 Hz), 7.65 (1H, d, J 8.7 Hz), 7.51 (1H, dd, J8.8 2.0 Hz), 6.88 (2H, d, J 9.1 Hz), 3.50 (4H, q, J 7.0 Hz), 2.70-2.64(1H, m), 1.24-1.17 (12H, m)

N-(2-(4-(Diethylamino)phenyl)benzo[d]oxazol-5-yl)thiophene-2-carboxamide

LCMS RT=7.77 min, MH⁺ 392.1; ¹H NMR (DMSO): 10.41 (1H, s), 8.14 (1H, d,J 1.8 Hz), 8.12 (1H, dd, J 3.8 1.0 Hz), 8.04 (2H, d, J 9.1 Hz), 7.95(1H, dd, J 4.9 1.0 Hz), 7.73 (1H, d, J 8.6 Hz), 7.66 (1H, dd, J 8.7 1.9Hz), 7.34-7.30 (1H, m), 6.90 (2H, d, J 9.2 Hz), 3.51 (4H, q, J 7.0 Hz),1.22 (6H, t, J 7.0 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)isonicotinamide

LCMS RT=6.36 min, MH⁺ 350.0; ¹H NMR (DMSO): 10.71 (1H, s), 8.82 (2H, d,J 9.0 Hz), 8.32-8.30 (1H, m), 8.22 (2H, d, J 8.6 Hz), 7.90 (2H, d, J 6.0Hz), 7.85-7.79 (2H, m), 7.71 (2H, d, J 8.6 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=7.67 min, MH⁺ 349.0; ¹H NMR (DMSO): 10.46 (1H, s), 8.32 (1H, s),8.22 (2H, d, J 8.5 Hz), 8.01-7.98 (2H, m), 7.79 (2H, d, J 1.1 Hz), 7.71(2H, d, J 8.6 Hz), 7.65-7.50 (3H, m)

4-Chloro-N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=8.51 min, MH⁺ 383.2; ¹H NMR (DMSO): 10.52 (1H, s), 8.30 (1H, s),8.22 (2H, d, J 8.8 Hz), 8.03 (2H, d, J 8.8 Hz), 7.82-7.77 (2H, m), 7.71(2H, d, J 8.4 Hz), 7.64 (2H, d, J 8.4 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-4-methylbenzamide

LCMS RT=8.21 min, MH⁺ 362.8; ¹H NMR (DMSO): 10.36 (1H, s), 8.31 (1H, s),8.22 (2H, d, J 8.7 Hz), 7.92 (2H, d, J 8.2 Hz), 7.78 (2H, d, J 1.3 Hz),7.71 (2H, d, J 8.7 Hz), 7.37 (2H, d, J 8.0 Hz), 2.41 (3H, s)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-4-methoxybenzamide

LCMS RT=7.62 min, MH⁺ 378.7; ¹H NMR (DMSO): 10.28 (1H, s), 8.30 (1H, s),8.22 (2H, d, J 8.9 Hz), 7.99 (2H, d, J 8.9 Hz), 7.77 (2H, s), 7.70 (2H,d, J 8.3 Hz), 7.08 (2H, d, J 8.9 Hz), 3.86 (3H, s)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-2-methoxybenzamide

LCMS RT=8.55 min, MH⁺ 379.0; ¹H NMR (DMSO): 10.29 (1H, s), 8.29 (1H, d,J 1.5 Hz), 8.18 (2H, d, J 8.6 Hz), 7.77-7.62 (5H, m), 7.52-7.46 (1H, m),7.17 (1H, d, J 8.3 Hz), 7.05 (1H, t, J 7.5 Hz), 3.89 (3H, s)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-4-(dimethylamino)benzamide

LCMS RT=7.96 min, MH⁺ 392.3; ¹H NMR (DMSO): 10.12 (1H, s), 8.36 (1H, s),8.27 (2H, d, J 8.6 Hz), 7.96 (2H, d, J 8.8 Hz), 7.83-7.81 (2H, m), 7.76(2H, d, J 8.5 Hz), 6.84 (2H, d, J 9.0 Hz), 3.07 (6H, s)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-4-(trifluoromethyl)benzamide

LCMS RT=8.65 min, MH⁺ 416.7; ¹H NMR (DMSO): 10.67 (1H, s), 8.32 (1H, s),8.24-8.18 (4H, m), 7.95 (2H, d, J 8.6 Hz), 7.84-7.77 (2H, m), 7.71 (2H,d, J 8.6 Hz)

3,5-Dichloro-N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)benzamide

LCMS RT=10.09 min, MH⁺ 417.1; ¹H NMR (DMSO): 10.68 (1H, s), 8.34 (1H, d,J 1.8 Hz), 8.28 (2H, d, J 8.6 Hz), 8.08 (2H, d, J 1.9 Hz), 7.96 (1H, t,J 1.9 Hz), 7.89-7.78 (2H, m), 7.76 (2H, d, J 8.7 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-4-fluorobenzamide

LCMS RT=7.78 min, MH⁺ 367.3; ¹H NMR (DMSO): 10.58 (1H, s), 8.35 (1H, s),8.28 (2H, d, J 8.9 Hz), 8.16-8.11 (2H, m), 7.90-7.82 (2H, m), 7.77 (2H,d, J 8.4 Hz), 7.52-7.42 (2H, m)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-2-phenylacetamide

LCMS RT=7.48 min, MH⁺ 362.8; ¹H NMR (DMSO): 10.38 (1H, s), 8.22-8.17(3H, m), 7.75-7.65 (3H, m), 7.55 (1H, dd, J 9.0 2.1 Hz), 7.38-7.24 (5H,m), 3.69 (2H, s)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-3-phenylpropanamide

LCMS RT=7.92 min, MH⁺ 377.3; ¹H NMR (DMSO): 10.12 (1H, s), 8.19 (2H, d,J 8.8 Hz), 8.16 (1H, d, J 1.8 Hz), 7.74-7.68 (3H, m), 7.51 (1H, dd, J8.8 2.0 Hz), 7.33-7.17 (5H, m), 2.95 (2H, t, J 7.3 Hz), 2.67 (2H, t, J7.3 Hz),

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=7.04 min, MH⁺ 315.1; ¹H NMR (DMSO): 10.07 (1H, s), 8.21-8.18(3H, m), 7.73-7.67 (3H, m), 7.54 (1H, dd, J 8.8 1.9 Hz), 2.32 (2H, t, J7.4 Hz), 1.72-1.58 (2H, m), 0.94 (3H, t, J 7.4 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)pentanamide

LCMS RT=7.66 min, MH⁺ 329.1; ¹H NMR (DMSO): 10.07 (1H, s), 8.22-8.16(3H, m), 7.73-7.68 (3H, m), 7.56-7.51 (1H, m), 2.34 (2H, t, J 7.5 Hz),1.66-1.56 (2H, m), 1.42-1.30 (2H, m), 0.92 (3H, t, J 7.2 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.04 min, MH⁺ 315.1; ¹H NMR (DMSO): 10.03 (1H, s), 8.22-8.18(3H, m), 7.74-7.67 (3H, m), 7.56 (1H, dd, J 8.9 2.1 Hz), 2.67-2.59 (1H,m), 1.14 (6H, d, J 6.8 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)furan-2-carboxamide

LCMS RT=7.01 min, MH⁺ 338.9; ¹H NMR (DMSO): 10.40 (1H, s), 8.27 (1H, d,J 1.1 Hz), 8.22 (2H, d, J 8.5 Hz), 7.97 (1H, s), 7.78 (2H, s), 7.70 (2H,d, J 8.5 Hz), 7.36 (1H, d, J 3.4 Hz), 6.74-6.73 (1H, m)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)thiophene-2-carboxamide

LCMS RT=7.54 min, MH⁺ 355.0; ¹H NMR (DMSO): 10.42 (1H, s), 8.25-8.21(3H, m), 8.06 (1H, dd, J 3.9 1.2 Hz), 7.89 (1H, dd, J 5.0 1.0 Hz), 7.80(1H, d, J 8.8 Hz), 7.74-7.69 (3H, m), 7.26 (1H, dd, J 5.0 3.8 Hz)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)nicotinamide

LCMS RT=6.12 min, MH⁺ 330.1; ¹H NMR (DMSO): 10.62 (1H, s), 9.15 (1H, dd,J 2.1 0.7 Hz), 8.79 (1H, dd, J 4.8 1.7 Hz), 8.34 (1H, dt, J 7.9 1.8 Hz),8.27 (1H, d, J 1.6 Hz), 8.11 (2H, d, J 8.2 Hz), 7.82-7.72 (2H, m),7.63-7.58 (1H, m), 7.44 (2H, d, J 8.0 Hz), 2.43 (3H, s)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)isonicotinamide

LCMS RT=6.17 min, MH⁺ 330.1; ¹H NMR (DMSO): 10.68 (1H, s), 8.82 (2H, d,J 6.0 Hz), 8.27 (1H, d, J 1.5 Hz), 8.22 (2H, d, J 8.2 Hz), 7.90 (2H, d,J 6.0 Hz), 7.81-7.72 (2H, m), 7.45 (2H, d, J 8.0 Hz), 2.43 (3H, s)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)propionamide

LCMS RT=6.34 min, MH⁺ 281.0; ¹H NMR (DMSO): 10.03 (1H, s), 8.14 (1H, d,J 1.8 Hz), 8.08 (2H, d, J 8.2 Hz), 7.69 (1H, d, J 8.8 Hz), 7.51 (1H, dd,J 8.8 2.0 Hz), 7.44 (2H, d, J 8.0 Hz), 2.42 (3H, s), 2.36 (2H, q, J 7.5Hz), 1.12 (3H, t, J 7.6 Hz)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)butyramide

LCMS RT=6.73 min, MH⁺ 295.1; ¹H NMR (DMSO): 10.04 (1H, s), 8.13 (1H, d,J 1.8 Hz), 8.08 (2H, d, J 8.2 Hz), 7.69 (1H, d, J 8.8 Hz), 7.51 (1H, dd,J 8.8 2.0 Hz), 7.43 (2H, d, J 8.0 Hz), 2.42 (3H, s), 2.32 (2H, t, J 7.4Hz), 1.71-1.58 (2H, m), 0.94 (3H, t, J 7.4 Hz)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)pentanamide

LCMS RT=7.20 min, MH⁺ 309.1; ¹H NMR (DMSO): 10.04 (1H, s), 8.13 (1H, d,J 1.8 Hz), 8.08 (2H, d, J 8.2 Hz), 7.68 (1H, d, J 8.8 Hz), 7.51 (1H, dd,J 8.8 2.0 Hz), 7.43 (2H, d, J 8.0 Hz), 2.42 (3H, s), 2.34 (2H, t, J 7.4Hz), 1.67-1.56 (2H, m), 1.41-1.29 (2H, m), 0.92 (3H, t, J 7.4 Hz)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.74 min, MH⁺ 295.1; ¹H NMR (DMSO): 10.00 (1H, s), 8.15 (1H, d,J 1.8 Hz), 8.09 (2H, d, J 8.2 Hz), 7.69 (1H, d, J 8.8 Hz), 7.53 (1H, dd,J 8.8 2.0 Hz), 7.43 (2H, d, J 8.0 Hz), 2.66-2.60 (1H, m), 2.42 (3H, s),1.13 (6H, d, J 6.8 Hz)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)furan-2-carboxamide

LCMS RT=6.71 min, MH⁺ 319.0; ¹H NMR (DMSO): 10.37 (1H, s), 8.23 (1H, s),8.10 (2H, d, J 8.2 Hz), 7.98-7.96 (1H, m), 7.75 (2H, d, J 1.0 Hz), 7.44(2H, d, J 8.0 Hz), 7.36 (1H, d, J 3.6 Hz), 6.74-6.72 (1H, m), 2.43 (3H,s)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)thiophene-2-carboxamide

LCMS RT=7.15 min, MH⁺ 335.0; ¹H NMR (DMSO): 10.40 (1H, s), 8.21 (1H, d,J 1.7 Hz), 8.11 (2H, d, J 8.2 Hz), 8.05 (1H, dd, J 3.8 1.0 Hz), 7.89(1H, d, J 4.9 1.0 Hz), 7.76 (1H, d, J 8.8 Hz), 7.69 (1H, dd, J 8.9 2.0Hz), 7.44 (2H, d, J 8.0 Hz), 7.26 (1H, dd, J 5.0 3.8 Hz), 2.43 (3H, s)

N-(2-(4-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)nicotinamide

LCMS RT=6.49 min, MH⁺ 383.9; ¹H NMR (DMSO): 10.70 (1H, s), 9.20-9.18(1H, m), 8.82 (1H, dd, J 4.6 1.5 Hz), 8.46 (2H, d, J 8.1 Hz), 8.40-8.36(2H, m), 8.04 (2H, d, J 8.0 Hz), 7.92-7.82 (2H, m), 7.66-7.61 (1H, m)

N-(2-(4-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)isonicotinamide

LCMS RT=6.52 min; ¹H NMR (DMSO): 10.80 (1H, s), 8.90 (2H, d, J 6.0 Hz),8.51 (2H, d, J 8.2 Hz), 8.44 (1H, d, J 1.6 Hz), 8.09 (2H, d, J 8.2 Hz),8.01-7.93 (3H, m), 7.89 (1H, dd, J 8.9 1.9 Hz)

N-(2-(4-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)acetamide

LCMS RT=6.30 min, MH⁺ 320.7; ¹H NMR (DMSO): 10.17 (1H, s), 8.40 (2H, d,J 8.7 Hz), 8.22-8.19 (1H, m), 7.99 (2H, d, J 8.5 Hz), 7.77 (1H, d, J 8.7Hz), 7.58-7.53 (1H, m), 2.09 (3H, s)

N-(2-(4-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)propionamide

LCMS RT=6.73 min, MH⁺ 335.0; ¹H NMR (DMSO): 10.09 (1H, s), 8.40 (2H, d,J 7.8 Hz), 8.23 (1H, d, J 1.9 Hz), 7.99 (2H, d, J 8.2 Hz), 7.77 (1H, d,J 8.7 Hz), 7.57 (1H, dd, J 8.8 2.0 Hz), 2.37 (2H, q, J 7.5 Hz), 1.12(3H, t, J 7.5 Hz)

N-(2-(4-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=7.18 min, MH⁺ 348.9; ¹H NMR (DMSO): 10.10 (1H, s), 8.40 (2H, d,J 7.8 Hz), 8.23 (1H, d, J 1.9 Hz), 7.99 (2H, d, J 8.2 Hz), 7.77 (1H, d,J 8.7 Hz), 7.58 (1H, dd, J 8.8 2.0 Hz), 2.33 (2H, t, J 7.3 Hz),1.69-1.59 (2H, m), 0.94 (3H, t, J 7.6 Hz)

N-(2-(4-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)pentanamide

LCMS RT=7.74 min, MH⁺ 363.1; ¹H NMR (DMSO): 10.10 (1H, s), 8.40 (2H, d,J 7.8 Hz), 8.22 (1H, d, J 1.9 Hz), 7.99 (2H, d, J 8.2 Hz), 7.77 (1H, d,J 8.7 Hz), 7.57 (1H, dd, J 8.8 2.0 Hz), 2.36 (2H, t, J 7.3 Hz),1.66-1.58 (2H, m), 1.42-1.29 (2H, m), 0.92 (3H, t, J 7.6 Hz)

N-(2-(4-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.15 min, MH⁺ 349.1; ¹H NMR (DMSO): 10.09 (1H, s), 8.43 (2H, d,J 7.8 Hz), 8.27 (1H, d, J 1.9 Hz), 8.02 (2H, d, J 8.2 Hz), 7.80 (1H, d,J 8.7 Hz), 7.63 (1H, dd, J 8.8 2.0 Hz), 2.72-2.63 (1H, m), 1.18 (6H, d,J 6.8 Hz)

N-(2-(4-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)furan-2-carboxamide

LCMS RT=7.15 min, MH⁺ 373.0; ¹H NMR (DMSO): 10.28 (1H, s), 8.27 (2H, d,J 8.0 Hz), 8.18-8.16 (1H, m), 7.86 (2H, d, J 8.2 Hz), 7.84-7.82 (1H, m),7.69-7.67 (2H, m), 7.23 (1H, dd, J 3.5 0.8 Hz), 6.59 (1H, dd, J 3.5 1.7Hz)

N-(2-(4-Methoxyphenyl)benzo[d]oxazol-5-yl)isonicotinamide

LCMS RT=5.76 min, MH⁺ 346.0; ¹H NMR (DMSO): 10.66 (1H, s), 8.81 (2H, d,J 6.1 Hz), 8.24 (1H, d, J 1.7 Hz), 8.16 (2H, d, J 9.0 Hz), 7.90 (2H, d,J 6.1 Hz), 7.77 (1H, d, J 8.8 Hz), 7.72 (1H, dd, J 8.8 1.9 Hz), 7.18(2H, d, J 8.9 Hz), 3.88 (3H, s)

N-(2-(4-Methoxyphenyl)benzo[d]oxazol-5-yl)acetamide

LCMS RT=5.59 min, MH⁺ 283.0; ¹H NMR (DMSO): 10.09 (1H, s), 8.13 (2H, d,J 8.9 Hz), 8.08 (1H, d, J 1.8 Hz), 7.67 (1H, d, J 8.9 Hz), 7.47 (1H, dd,J 8.8 2.0 Hz), 7.16 (2H, d, J 9.0 Hz), 3.87 (3H, s), 2.08 (3H, s)

N-(2-(4-Methoxyphenyl)benzo[d]oxazol-5-yl)propionamide

LCMS RT=5.89 min, MH⁺ 297.1; ¹H NMR (DMSO): 10.02 (1H, s), 8.15-8.10(3H, m), 7.67 (1H, d, J 8.7 Hz), 7.49 (1H, dd, J 8.8 1.8 Hz), 7.16 (2H,d, J 8.8 Hz), 3.88 (3H, s), 2.36 (2H, q, J 7.7 Hz), 1.11 (3H, t, J 7.5Hz)

N-(2-(4-Methoxyphenyl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=6.19 min, MH⁺ 311.1; ¹H NMR (DMSO): 10.02 (1H, s), 8.13 (2H, d,J 9.0 Hz), 8.10 (1H, d, J 1.9 Hz), 7.66 (1H, d, J 8.9 Hz), 7.49 (1H, dd,J 8.8 1.8 Hz), 7.16 (2H, d, J 9.0 Hz), 3.87 (3H, s), 2.32 (2H, t, J 7.3Hz), 1.70-1.58 (2H, m), 0.94 (3H, t, J 7.5 Hz)

N-(2-(4-Methoxyphenyl)benzo[d]oxazol-5-yl)pentanamide

LCMS RT=6.59 min, MH⁺ 325.1; ¹H NMR (DMSO): 10.02 (1H, s), 8.13 (2H, d,J 9.0 Hz), 8.10 (1H, d, J 1.9 Hz), 7.66 (1H, d, J 8.9 Hz), 7.49 (1H, dd,J 8.8 1.8 Hz), 7.16 (2H, d, J 9.0 Hz), 3.87 (3H, s), 2.34 (2H, t, J 7.3Hz), 1.66-1.56 (2H, m), 1.41-1.29 (2H, m), 0.92 (3H, t, J 7.5 Hz)

N-(2-(4-Methoxyphenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.19 min, MH⁺ 311.1; ¹H NMR (DMSO): 9.98 (1H, s), 8.15-8.11 (3H,m), 7.66 (1H, d, J 8.9 Hz), 7.51 (1H, dd, J 8.8 1.8 Hz), 7.16 (2H, d, J9.0 Hz), 3.88 (3H, s), 1.13 (6H, d, J 6.9 Hz)

N-(2-(4-Methoxyphenyl)benzo[d]oxazol-5-yl)furan-2-carboxamide

LCMS RT=6.16 min, MH⁺ 335.1; ¹H NMR (DMSO): 10.36 (1H, s), 8.20-8.13(3H, m), 7.96 (1H, dd, J 1.8 0.8 Hz), 7.72 (2H, d, J 1.2 Hz), 7.36 (1H,dd, J 3.5 0.8 Hz), 7.17 (2H, d, J 9.0 Hz), 6.73 (1H, dd, J 3.5 1.7 Hz),3.88 (3H, s)

N-(2-(4-Methoxyphenyl)benzo[d]oxazol-5-yl)thiophene-2-carboxamide

LCMS RT=6.54 min, MH⁺ 351.0; ¹H NMR (DMSO): 10.38 (1H, s), 8.19-8.14(3H, m), 8.05 (1H, dd, J 3.7 1.0 Hz), 7.88 (1H, dd, J 4.1 1.0 Hz), 7.74(1H, d, J 8.8 Hz), 7.67 (1H, dd, J 8.8 2.0 Hz), 7.27-7.23 (1H, m), 7.17(2H, d, J 8.9 Hz), 3.88 (3H, s)

N-(2-m-Tolylbenzo[d]oxazol-5-yl)butyramide

LCMS RT=6.67 min, MH⁺ 295.0;

N-(2-(3-(Dimethylamino)phenyl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=6.62 min, MH⁺ 324.1; ¹H NMR (DMSO): 10.06 (1H, s), 8.13 (1H, d,J 1.8 Hz), 7.70 (1H, d, J 8.8 Hz), 7.53 (1H, dd, J 8.8 2.0 Hz),7.49-7.37 (3H, m), 7.00-6.96 (1H, m), 3.00 (6H, s), 2.32 (2H, t, J 7.6Hz), 1.71-1.55 (2H, m), 0.94 (3H, t, J 7.4 Hz)

N-(2-m-Tolylbenzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.64 min, MH⁺ 295.0; ¹H NMR (DMSO): 10.02 (1H, s), 8.17 (1H, d,J 1.9 Hz), 8.03-7.98 (2H, m), 7.71 (1H, d, J 8.8 Hz), 7.56-7.44 (3H, m),2.60-2.58 (1H, m), 2.44 (3H, s), 1.14 (6H, d, J 6.8 Hz)

N-(2-(3-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.88 min, MH⁺ 349.0; ¹H NMR (DMSO): 10.06 (1H, s), 8.51-8.43(2H, m), 8.23 (1H, s), 8.03 (1H, d, J 7.4 Hz), 7.91-7.85 (1H, m), 7.77(1H, d, J 8.5 Hz), 7.62-7.57 (1H, m), 2.63 (1H, t, J 6.8 Hz), 1.14 (6H,d, J 6.8 Hz)

N-(2-(3-(Dimethylamino)phenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.59 min, MH⁺ 324.1; ¹H NMR (DMSO): 10.01 (1H, s), 8.15 (1H, d,J 1.8 Hz), 7.70 (1H, d, J 8.8 Hz), 7.55 (1H, dd, J 8.8 2.0 Hz),7.49-7.37 (3H, m), 7.00-6.96 (1H, m), 3.01 (6H, s), 2.65-2.58 (1H, m),1.13 (6H, d, J 7.0 Hz)

N-(2-(3-(Trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=6.85 min, MH⁺ 349.0; ¹H NMR (DMSO): 10.08 (1H, s), 8.48 (1H, d,J 7.8 Hz), 8.43 (1H, s), 8.21 (1H, d, J 1.9 Hz), 8.02 (1H, d, J 8.0 Hz),7.88 (1H, d, J 7.7 Hz), 7.76 (1H, d, J 8.8 Hz), 7.58 (1H, dd, J 8.8 2.0Hz), 2.33 (2H, t, J 7.4 Hz), 1.71-1.59 (2H, m), 0.95 (3H, t, J 7.4 Hz)

N-(2-o-Tolylbenzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.62 min, MH⁺ 295.1; ¹H NMR (DMSO): 10.00 (1H, s), 8.19 (1H, d,J 1.9 Hz), 8.12 (1H, dd, J 7.4 1.5 Hz), 7.71 (1H, d, J 8.8 Hz),7.57-7.40 (4H, m), 2.75 (3H, s), 2.65-2.59 (1H, m), 1.14 (6H, d, J 6.7Hz)

N-(2-(2-Chlorophenyl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=6.42 min, MH⁺ 315.0; ¹H NMR (DMSO): 10.08 (1H, s), 8.22 (1H, d,J 1.8 Hz), 8.15 (1H, dd, J 7.6 1.8 Hz), 7.76-7.55 (5H, m), 2.34 (2H, t,J 7.4 Hz), 1.71-1.59 (2H, m), 0.95 (3H, t, J 7.4 Hz)

N-(2-(2-Chlorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.41 min, MH⁺ 315.0; ¹H NMR (DMSO): 10.03 (1H, s), 8.23 (1H, d,J 1.8 Hz), 8.15 (1H, dd, J 7.6 1.7 Hz), 7.71-7.55 (5H, m), 2.68-2.58(1H, m), 1.14 (6H, d, J 6.7 Hz)

N-(2-(3-Chlorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.89 min, MH⁺ 315.0; ¹H NMR (DMSO): 10.05 (1H, s), 8.21-8.15(3H, m), 7.75-7.63 (3H, m), 7.57 (1H, d, J 8.8 2.0 Hz), 2.62-2.58 (1H,m), 1.14 (6H, d, J 6.8 Hz)

N-(2-(3-chlorophenyl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=6.89 min, MH⁺ 315.1; ¹H NMR (DMSO): 10.07 (1H, s), 8.19-8.11(3H, m), 7.75-7.63 (3H, m), 7.56 (1H, d, J 8.8 2.0 Hz), 2.33 (2H, t, J7.4 Hz), 1.71-1.59 (2H, m), 0.94 (3H, t, J 7.4 Hz)

Method 3C (Compounds II)

As Method 3A, except instead of diisopropylamine in dichloromethane,pyridine was used both as solvent and base.

N-(2-Phenyloxazolo[5,4-b]pyridin-6-yl)butyramide

LCMS RT=5.95 min, MH⁺ 282.0; ¹H NMR (DMSO): 10.31 (1H, s), 8.54 (1H, d,J 2.3 Hz), 8.48 (1H, d, J 2.3 Hz), 8.24-8.21 (2H, m), 7.72-7.62 (3H, m),2.37 (2H, t, J 7.3 Hz), 1.72-1.60 (2H, m), 0.95 (3H, t, J 7.5 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)propionamide

LCMS RT=6.54 min, MH⁺ 301.0; ¹H NMR (DMSO): 10.07 (1H, s), 8.21-8.18(3H, m), 7.73-7.67 (3H, m), 7.53 (1H, dd, J 8.8 2.0 Hz), 2.36 (2H, q, J7.6 Hz), 1.12 (3H, t, J 7.5 Hz)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)pivalamide

LCMS RT=6.94 min, MH⁺ 309.1; ¹H NMR (DMSO): 9.36 (1H, s), 8.13 (1H, d, J1.8 Hz), 8.09 (2H, d, J 8.2 Hz), 7.69 (1H, d, J 8.8 Hz), 7.61 (1H, dd, J8.8 2.0 Hz), 7.43 (2H, d, J 8.0 Hz), 2.42 (3H, s), 1.26 (9H, s)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)pivalamide

LCMS RT=7.28 min, MH⁺ 329.1; ¹H NMR (DMSO): 9.39 (1H, s), 8.20 (2H, d, J8.6 Hz), 8.17 (1H, d, J 1.7 Hz), 7.74-7.62 (4H, m), 1.26 (9H, s)

N-(2-Benzylbenzo[d]oxazol-5-yl)butyramide

LCMS RT=5.98 min, MH⁺ 295.1; ¹H NMR (DMSO): 9.97 (1H, s), 8.03 (1H, d, J1.8 Hz), 7.56 (1H, d, J 8.7 Hz), 7.44 (1H, dd, J 8.9 2.1 Hz), 7.38-7.35(4H, m), 7.33-7.25 (1H, m), 4.31 (2H, s), 2.28 (2H, t, J 7.3 Hz),1.69-1.53 (2H, m), 0.92 (3H, t, J 7.5 Hz)

N-(2-Benzylbenzo[d]oxazol-5-yl)isobutyramide

LCMS RT=5.96 min, MH⁺ 295.1; ¹H NMR (DMSO): 9.93 (1H, s), 8.04 (1H, d, J2.1 Hz), 7.56 (1H, d, J 8.9 Hz), 7.47 (1H, dd, J 9.0 2.0 Hz), 7.38-7.35(4H, m), 7.33-7.28 (1H, m), 4.31 (2H, s), 2.60-2.58 (1H, m), 1.11 (6H,d, J 6.8 Hz)

N-(2-p-Tolylbenzo[d]oxazol-4-yl)butyramide

LCMS RT=7.54 min, MH⁺ 295.1; ¹H NMR (DMSO): 10.03 (1H, s), 8.13 (2H, d,J 8.2 Hz), 8.03 (1H, d, J 8.2 Hz), 7.48-7.44 (3H, m), 7.34 (1H, t, J 8.2Hz), 2.43 (3H, s), 1.72-1.60 (2H, m), 1.09 (3H, t, J 6.9 Hz)

N-(2-p-Tolylbenzo[d]oxazol-4-yl)isobutyramide

LCMS RT=7.51 min, MH⁺ 295.1; ¹H NMR (DMSO): 9.78 (1H, s), 7.93 (2H, d, J8.4 Hz), 7.83 (1H, d, J 8.2 Hz), 7.28-7.23 (3H, m), 7.14 (1H, t, J 8.4Hz), 2.22 (3H, s), 0.94 (6H, d, J 6.8 Hz)

N-(2-Cyclohexylbenzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.48 min, MH⁺ 287.1; ¹H NMR (CDCl₃): 7.82 (1H, d, J 1.7 Hz),7.66-7.56 (1H, m), 7.46 (1H, d, J 8.8 Hz), 7.30-7.25 (1H, m), 3.07-2.97(1H, m), 2.65-2.53 (1H, m), 2.26-2.16 (2H, m), 1.97-1.72 (5H, m),1.56-1.37 (3H, m), 1.33 (6H, t, J 6.8 Hz)

N-(2-Cyclohexylbenzo[d]oxazol-5-yl)butyramide

LCMS RT=6.51 min, MH⁺ 287.2; ¹H NMR (CDCl₃): 7.69 (1H, s), 7.45 (1H, d,J 8.8 Hz), 7.33 (1H, d, J 8.8 Hz), 7.16 (1H, s), 2.93-2.83 (1H, m), 2.29(2H, t, J 7.6 Hz), 2.11-2.06 (2H, m), 1.83-1.57 (6H, m), 1.43-1.18 (4H,m), 0.95 (3H, t, J 7.5 Hz)

N-(2-(2,4-Dichlorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.17 min, MH⁺ 348.9; ¹H NMR (DMSO): 10.11 (1H, s), 8.23 (1H, d,J 1.7 Hz), 8.19 (1H, d, J 8.8 Hz), 7.92 (1H, d, J 2.1 Hz), 7.75 (1H, d,J 9.0 Hz), 7.68 (1H, dd, J 8.5 2.1 Hz), 7.60 (1H, dd, J 8.7 2.0 Hz),2.64 (1H, t, J 6.8 Hz), 1.14 (6H, d, J 6.8 Hz)

N-(2-(4-Fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.39 min, MH⁺ 299.0; ¹H NMR (DMSO): 10.00 (1H, s), 8.27-8.23(2H, m), 8.18-8.17 (1H, m), 7.70 (1H, d, J 8.6 Hz), 7.55 (1H, dd, J 8.72.0 Hz), 7.46 (2H, t, J 8.7 Hz), 2.64-2.59 (1H, m), 1.14 (6H, d, J 6.8Hz)

N-(2-(3,4-Dichlorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.55 min, MH⁺ 349.5; ¹H NMR (DMSO): 10.03 (1H, s), 8.35 (1H, d,J 1.9 Hz), 8.21 (1H, d, J 1.9 Hz), 8.15 (1H, d, J 8.4 2.0 Hz), 7.89 (1H,d, J 8.4 Hz), 7.74 (1H, d, J 8.9 Hz), 7.58 (1H, dd, J 8.9 2.0 Hz),2.67-2.60 (1H, m), 1.14 (6H, d, J 6.8 Hz)

N-(2-(5-Chloropyridin-2-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=5.95 min, MH⁺ 316.0; ¹H NMR (DMSO): 10.05 (1H, s), 8.86 (1H, d,J 2.1 Hz), 8.35 (1H, d, J 8.5 Hz), 8.25 (1H, d, J 1.7 Hz), 8.19 (1H, dd,J 8.5 2.4 Hz), 7.77 (1H, d, J 8.8 Hz), 7.60 (1H, dd, J 8.8 2.0 Hz),2.65-2.61 (1H, m), 1.14 (6H, d, J 6.7 Hz)

N-(2-(3,5-Dichlorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.83 min, MH⁺ 348.7; ¹H NMR (DMSO): 10.05 (1H, s), 8.23 (1H, d,J 1.9 Hz), 8.15 (2H, d, J 2.0 Hz), 7.92 (1H, t, J 2.0 Hz), 7.75 (1H, d,J 8.8 Hz), 7.60 (1H, dd, J 8.9 2.0 Hz), 2.68-2.60 (1H, m), 1.14 (6H, d,J 6.8 Hz)

N-(2-(2,3-Dichlorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.80 min, MH⁺ 348.9; ¹H NMR (DMSO): 10.04 (1H, s), 8.24 (1H, d,J 1.8 Hz), 8.11 (1H, dd, J 7.9 1.6 Hz), 7.93 (1H, dd, J 8.1 1.6 Hz),7.76 (1H, d, J 8.8 Hz), 7.63-7.59 (2H, m), 2.70-2.58 (1H, m), 1.14 (6H,d, J 6.8 Hz)

N-(2-Phenethylbenzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.22 min, MH⁺ 309.1; ¹H NMR (DMSO): 9.92 (1H, s), 8.03 (1H, d, J1.8 Hz), 7.57 (1H, d, J 8.8 Hz), 7.46 (1H, dd, J 8.7 2.0 Hz), 7.29-7.27(4H, m), 7.23-7.16 (1H, m), 3.21-3.10 (4H, m), 1.12 (6H, d, J 6.7 Hz)

N-(2-(1-Phenylethyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.23 min, MH⁺ 309.1; ¹H NMR (DMSO): 9.93 (1H, s), 8.06 (1H, d, J1.9 Hz), 7.54 (1H, d, J 8.8 Hz), 7.47 (1H, dd, J 8.8 2.1 Hz), 7.36-7.32(4H, m), 7.30-7.24 (1H, m), 4.51 (1H, q, J 7.1 Hz), 2.65-2.57 (1H, m),1.71 (3H, d, J 7.2 Hz), 1.12 (6H, d, J 6.8 Hz)

N-(2-(2,5-Dichlorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.10 min, MH⁺ 349.0; ¹H NMR (DMSO): 10.11 (1H, s), 8.31 (1H, d,J 1.8 Hz), 8.25 (1H, dd, J 2.4 0.5 Hz), 7.83 (2H, d, J 8.7 Hz), 7.80(1H, dd, J 8.7 2.5 Hz), 7.67 (1H, dd, J 8.9 2.0 Hz), 2.74-2.64 (1H, m),1.20 (6H, d, J 6.8 Hz)

N-(2-(2-Chloro-4-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.59 min, MH⁺ 333.0; ¹H NMR (DMSO): 10.05 (1H, s), 8.30-8.20(2H, m), 7.77-7.73 (2H, m), 7.59 (1H, dd, J 8.8 2.0 Hz), 7.51-7.45 (1H,m), 2.68-2.57 (1H, m), 1.14 (6H, d, J 6.8 Hz)

N-(2-(2-Chloro-6-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.29 min, MH⁺ 333.1; ¹H NMR (DMSO): 10.08 (1H, s), 8.26 (1H, d,J 1.9 Hz), 7.80-7.71 (2H, m), 7.64-7.60 (2H, m), 7.57-7.50 (1H, m),2.68-2.58 (1H, m), 1.14 (6H, d, J 6.9 Hz)

N-(2-(3-Chloro-2-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.65 min, MH⁺ 333.1; ¹H NMR (DMSO): 10.06 (1H, s), 8.31-8.16(2H, m), 7.88 (1H, dt, J 8.4 1.7 Hz), 7.77 (1H, d, J 8.8 Hz), 7.60 (1H,dd, J 8.9 2.0 Hz), 7.47 (1H, dt, J 8.0 1.0 Hz), 2.66-2.60 (1H, m), 1.14(6H, d, J 6.7 Hz)

N-(2-(4-Chloro-2-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.69 min, MH⁺ 333.1; ¹H NMR (DMSO): 10.05 (1H, s), 8.28-8.21(2H, m), 7.79-7.73 (2H, m), 7.60-7.53 (2H, m), 2.67-2.58 (1H, m), 1.14(6H, d, J 6.7 Hz)

N-(2-(2-Chloro-5-fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.54 min, MH⁺ 333.1; ¹H NMR (DMSO): 10.07 (1H, s), 8.25 (1H, d,J 1.9 Hz), 7.99 (1H, dd, J 9.2 3.2 Hz), 7.80-7.75 (2H, m), 7.63-7.52(2H, m), 2.68-2.59 (1H, m), 1.14 (6H, d, J 6.7 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)cyclopentanecarboxamide

LCMS RT=7.52 min, MH⁺ 341.0; ¹H NMR (DMSO): 10.08 (1H, s), 8.20-8.16(3H, m), 7.73-7.66 (3H, m), 7.55 (1H, dd, J 8.8 2.0 Hz), 2.85-2.75 (1H,m), 1.93-1.57 (8H, m)

N-(5-Chloro-2-(4-chlorophenyl)benzo[d]oxazol-6-yl)isobutyramide

LCMS RT=8.10 min; ¹H NMR (DMSO): 9.59 (1H, s), 8.20 (2H, d, J 8.8 Hz),8.12 (1H, s), 8.02 (1H, s), 7.71 (2H, d, J 8.6 Hz), 2.84-2.73 (1H, m),1.16 (6H, d, J 6.8 Hz)

N-(2-(Tetrahydro-2H-pyran-4-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=5.38 min, MH⁺ 289.0; ¹H NMR (DMSO): 9.95 (1H, s), 8.04 (1H, d, J1.9 Hz), 7.59 (1H, d, J 8.8 Hz), 7.48 (1H, dd, J 8.8 2.0 Hz), 3.95-3.88(2H, m), 3.47-3.43 (3H, m), 2.64-2.55 (1H, m), 2.06-1.99 (2H, m),1.89-1.75 (2H, m), 1.12 (6H, d, J 6.8 Hz)

N-(2-(3,4-Dichlorophenyl)benzo[d]oxazol-5-yl)cyclopropanecarboxamide

LCMS RT=6.99 min, MH⁺ 348.8; ¹H NMR (DMSO): 10.45 (1H, s), 8.30 (1H, dd,J 2.0 Hz), 8.15 (1H, d, J 1.9 Hz), 8.10 (1H, dd, J 8.4 2.0 Hz), 7.86(1H, d, J 8.4 Hz), 7.71 (1H, d, J 8.9 Hz), 7.53 (1H, dd, J 8.9 2.0 Hz),1.81-1.74 (1H, m), 0.82-0.76 (4H, m)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-6-yl)cyclopropanecarboxamide

LCMS RT=6.93 min, MH⁺ 312.9; ¹H NMR (DMSO): 10.53 (1H, s), 8.27 (1H, dd,J 1.7 Hz), 8.18 (2H, d, J 8.7 Hz), 7.74 (1H, d, J 8.7 Hz), 7.68 (2H, d,J 8.7 Hz), 7.44 (1H, dd, J 8.7 1.9 Hz), 1.86-1.78 (1H, m), 0.85-0.80(4H, m)

N-(2-(2,3-Dichlorophenyl)benzo[d]oxazol-6-yl)isobutyramide

LCMS RT=7.05 min; ¹H NMR (DMSO): 10.21 (1H, s), 8.34 (1H, d, J 1.8 Hz),8.11 (1H, dd, J 7.9 1.6 Hz), 7.92 (1H, dd, J 8.1 1.5 Hz), 7.81 (1H, d, J8.7 Hz), 7.60 (1H, t, J 8.0 Hz), 7.48 (1H, dd, J 8.7 1.9 Hz), 2.67-2.61(1H, m), 1.14 (6H, d, J 6.8 Hz)

N-(2-(4-(Trifluoromethoxy)phenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.04 min; ¹H NMR (DMSO): 10.05 (1H, s), 8.32 (2H, d, J 9.0 Hz),8.20 (1H, d, J 1.9 Hz), 7.74 (1H, d, J 8.9 Hz), 7.63-7.55 (3H, m),2.68-2.57 (1H, m), 1.14 (6H, d, J 6.8 Hz)

N-(2-Cyclopentylbenzo[d]oxazol-5-yl)isobutyramide

LCMS RT=5.23 min, MH⁺ 273.0; ¹H NMR (DMSO): 9.93 (1H, s), 8.01 (1H, d, J1.8 Hz), 7.57 (1H, d, J 8.7 Hz), 7.46 (1H, dd, J 8.8 1.8 Hz), 3.42-3.39(1H, m), 2.61-2.57 (1H, m), 2.15-2.04 (2H, m), 1.95-1.87 (2H, m),1.78-1.62 (4H, m), 1.12 (6H, d, J 6.8 Hz)

N-(4-(5-Acetamidobenzo[d]oxazol-2-yl)phenyl)acetamide

LCMS RT=5.08 min, MH⁺ 309.9; ¹H NMR (DMSO): 10.31 (1H, s), 10.11 (1H,s), 8.13-8.08 (3H, m), 7.82 (2H, d, J 8.7 Hz), 7.68 (1H, d, J 8.7 Hz),7.48 (1H, dd, J 8.8 2.0 Hz), 2.11 (3H, s), 2.08 (3H, s)

N-(2-(2-Chloro-3-(trifluoromethyl)phenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.78 min, MH⁺ 383.0; ¹H NMR (DMSO): 10.07 (1H, s), 8.40 (1H, dd,J 8.1 1.3 Hz), 8.27 (1H, d, J 1.8 Hz), 8.14 (1H, dd, J 7.9 1.3 Hz),7.82-7.77 (2H, m), 7.62 (1H, dd, J 8.8 2.1 Hz), 2.66-2.61 (1H, m), 1.14(6H, d, J 6.8 Hz)

N-(2-(3,4-Dichlorophenyl)benzo[d]oxazol-6-yl)isobutyramide

LCMS RT=7.82 min, MH⁺ 349.1; ¹H NMR (DMSO): 10.20 (1H, s), 8.33 (1H, d,J 2.0 Hz), 8.31 (1H, d, J 1.7 Hz), 8.14 (1H, dd, J 8.4 2.0 Hz), 7.88(1H, d, J 8.5 Hz), 7.75 (1H, d, J 8.8 Hz), 7.48 (1H, dd, J 8.7 1.9 Hz),2.68-2.60 (1H, m), 1.14 (6H, d, J 6.8 Hz)

N-(2-(Naphthalen-2-yl)benzo[d]oxazol-5-yl)acetamide

LCMS RT=6.45 min, MH⁺ 303.1; ¹H NMR (DMSO): 10.15 (1H, s), 8.84 (1H, s),8.27 (1H, dd, J 8.6 1.7 Hz), 8.20-8.13 (3H, m), 8.06-8.03 (1H, m), 7.76(1H, d, J 8.6 Hz), 7.71-7.63 (2H, m), 7.54 (1H, dd, J 8.8 2.1 Hz), 2.17(3H, s)

N-(2-(4-Acetamidophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=5.52 min, MH⁺ 338.0; ¹H NMR (DMSO): 10.46 (1H, s), 10.31 (1H,s), 8.15-8.11 (3H, m), 7.82 (2H, d, J 8.7 Hz), 7.67 (1H, d, J 8.7 Hz),7.52 (1H, dd, J 8.8 1.9 Hz), 2.67-2.58 (1H, m), 2.11 (3H, s), 1.13 (6H,d, J 6.9 Hz)

N-(2-(Naphthalen-2-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.10 min, MH⁺ 331.1; ¹H NMR (DMSO): 10.04 (1H, s), 8.84 (1H, s),8.28-8.12 (4H, m), 8.07-8.03 (1H, m), 7.76 (1H, d, J 8.9 Hz), 7.77-7.62(2H, m), 7.58 (1H, dd, J 8.8 2.1 Hz), 2.64 (1H, t, J 7.4 Hz), 1.15 (6H,d, J 6.9 Hz)

N-(2-(Naphthalen-2-yl)benzo[d]oxazol-5-yl)thiophene-2-carboxamide

LCMS RT=7.47 min, MH⁺ 370.8; ¹H NMR (DMSO): 10.44 (1H, s), 8.86 (1H, s),8.30-8.14 (4H, m), 8.08-8.04 (2H, m), 7.89 (1H, dd, J 5.0 1.0 Hz), 7.83(1H, d, J 8.8 Hz), 7.76-7.64 (3H, m), 7.28-7.25 (1H, m)

N-(2-(Naphthalen-1-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.25 min, MH⁺ 331.2; ¹H NMR (DMSO): 10.07 (1H, s), 9.42 (1H, dd,J 8.2 0.7 Hz), 8.45 (1H, dd, J 7.4 1.2 Hz), 8.29 (1H, d, J 1.9 Hz),8.26-8.21 (1H, m), 8.13-8.09 (1H, m), 7.81-7.66 (4H, m), 7.61 (1H, dd, J8.8 2.1 Hz), 2.70-2.61 (1H, m), 1.16 (6H, d, J 6.8 Hz)

N-(2-(Biphenyl-4-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.56 min, MH⁺ 357.3; ¹H NMR (DMSO): 10.03 (1H, s), 8.28 (2H, d,J 8.5 Hz), 8.20 (1H, d, J 2.0 Hz), 7.94 (2H, d, J 8.6 Hz), 7.82-7.78(2H, m), 7.74 (1H, d, J 8.8 Hz), 7.58-7.41 (4H, m), 2.68-2.59 (1H, m),1.15 (6H, d, J 6.8 Hz)

N-(2-(6-Methoxynaphthalen-2-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.02 min, MH⁺ 361.2; ¹H NMR (DMSO): 10.03 (1H, s), 8.75 (1H, d,J 0.8 Hz), 8.21 (2H, dd, J 8.9 1.6 Hz), 8.10 (1H, d, J 9.0 Hz), 8.02(1H, d, J 8.7 Hz), 7.73 (1H, d, J 8.7 Hz), 7.56 (1H, dd, J 8.8 2.0 Hz),7.46 (1H, d, J 2.3 Hz), 7.29 (1H, dd, J 8.8 2.5 Hz), 3.93 (3H, s),2.68-2.58 (1H, m), 1.15 (6H, d, J 6.8 Hz)

N-(2-(6-Bromonaphthalen-2-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=8.13 min, MH⁺ 411.1; ¹H NMR (DMSO): 10.06 (1H, s), 8.86 (1H, s),8.36 (1H, d, J 1.7 Hz), 8.31 (1H, d, J 8.7 1.7 Hz), 8.23 (1H, d, J 1.9Hz), 8.18 (1H, d, J 8.9 Hz), 8.13 (1H, d, J 8.7 Hz), 7.80-7.74 (2H, m),7.58 (1H, dd, J 8.9 2.2 Hz), 2.68-2.59 (1H, m), 1.15 (6H, d, J 6.8 Hz)

N-(2-(Quinolin-3-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.24 min, MH⁺ 332.2; ¹H NMR (DMSO): 10.08 (1H, s), 9.62 (1H, d,J 2.1 Hz), 9.22 (1H, d, J 1.9 Hz), 8.29-8.24 (2H, m), 8.15 (1H, d, J 8.6Hz), 7.95-7.90 (1H, m), 7.80-7.73 (2H, m), 7.61 (1H, dd, J 8.8 2.2 Hz),2.69-2.60 (1H, m), 1.15 (6H, d, J 6.9 Hz)

N-(2-(Quinolin-2-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.28 min, MH⁺ 332.2; ¹H NMR (DMSO): 10.09 (1H, s), 8.64 (1H, d,J 8.4 Hz), 8.45 (1H, d, J 8.5 Hz), 8.32 (1H, d, J 1.8 Hz), 8.22 (1H, d,J 8.7 Hz), 8.13 (1H, dd, J 8.5 0.9 Hz), 7.94-7.84 (2H, m), 7.78-7.73(1H, m), 7.63 (1H, dd, J 8.8 2.0 Hz), 2.69-2.60 (1H, m), 1.15 (6H, d, J6.8 Hz)

N-(2-(4-Cyclohexylphenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=8.87 min, MH⁺ 363.3; ¹H NMR (DMSO): 10.00 (1H, s), 8.15 (1H, d,J 1.9 Hz), 8.11 (2H, d, J 8.4 Hz), 7.69 (1H, d, J 8.7 Hz), 7.53 (1H, dd,J 8.8 2.1 Hz), 7.47 (2H, d, J 8.3 Hz), 2.67-2.58 (2H, m), 1.84-1.71 (5H,m), 1.52-1.23 (5H, m), 1.13 (6H, d, J 6.8 Hz)

N-(2-(Benzo[d][1,3]dioxol-5-yl)-5-chlorobenzo[d]oxazol-6-yl)isobutyramide

¹H NMR (DMSO): 9.56 (1H, s), 8.05 (1H, s), 7.94 (1H, s), 7.77 (1H, dd, J8.1 1.7 Hz), 7.64 (1H, d, J 1.6 Hz), 7.16 (1H, d, J 8.2 Hz), 6.19 (2H,s), 2.83-2.72 (1H, m), 1.15 (6H, d, J 6.8 Hz)

N-(2-(Furan-2-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=5.75 min, MH⁺ 271.1; ¹H NMR (DMSO): 9.95 (1H, s), 8.08 (1H, d, J1.8 Hz), 8.01 (1H, dd, J 1.7 0.7 Hz), 7.62 (1H, d, J 8.9 Hz), 7.47 (1H,dd, J 8.9 2.0 Hz), 7.39 (1H, dd, J 3.5 0.7 Hz), 6.75 (1H, dd, J 3.5 1.8Hz), 2.60-2.50 (1H, m), 1.07 (6H, d, J 6.8 Hz)

N-(4-(Naphtho[1,2-d]oxazol-2-yl)phenyl)isobutyramide

LCMS RT=7.49 min, MH⁺ 331.1; ¹H NMR (DMSO): 10.22 (1H, s), 8.45 (1H, d,J 8.1 Hz), 8.22 (2H, d, J 8.7 Hz), 8.13 (1H, d, J 8.5 Hz), 7.98 (2H, s),7.89 (2H, d, J 8.9 Hz), 7.77-7.70 (1H, m), 7.65-7.59 (1H, m), 2.69-2.60(1H, m), 1.14 (6H, d, J 6.7 Hz)

N-(4-(Benzo[d]oxazol-2-yl)phenyl)isobutyramide

LCMS RT=6.48 min, MH⁺ 281.1; ¹H NMR (DMSO): 10.23 (1H, s), 8.14 (2H, d,J 8.9 Hz), 7.86 (2H, d, J 8.8 Hz), 7.79-7.75 (2H, m), 7.42-7.38 (2H, m),2.70-2.60 (1H, m), 1.13 (6H, d, J 6.8 Hz)

Method 3D (Compounds II)

As Method 3A, except instead of diisopropylethylamine indichloromethane, pyridine in dichloromethane was used.

N-(2-(2-Fluorophenyl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=6.10 min, MH⁺ 299.0; ¹H NMR (DMSO): 10.07 (1H, s), 8.25-8.19(2H, m), 7.75 (1H, d, J 8.8 Hz), 7.72-7.66 (1H, m), 7.58-7.42 (3H, m),2.33 (2H, t, J 7.5 Hz), 1.71-1.59 (2H, m), 0.94 (3H, t, J 7.4 Hz)

N-(2-(2-Fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.09 min, MH⁺ 299.0; ¹H NMR (DMSO): 10.09 (1H, s), 8.31-8.25(2H, m), 7.81 (1H, d, J 8.8 Hz), 7.78-7.72 (1H, m), 7.64 (1H, d, J 8.71.8 Hz), 7.58-7.48 (2H, m), 2.74-2.65 (1H, m), 1.20 (6H, d, J 6.8 Hz)

N-(2-(3-Fluorophenyl)benzo[d]oxazol-5-yl)butyramide

LCMS RT=6.39 min, MH⁺ 299.0; ¹H NMR (DMSO): 10.12 (1H, s), 8.24 (1H, d,J 1.9 Hz), 8.12-8.08 (1H, m), 8.02-7.97 (1H, m), 7.79 (1H, d, J 8.8 Hz),7.75-7.70 (1H, m), 7.63-7.53 (2H, m), 2.38 (2H, t, J 7.4 Hz), 1.77-1.64(2H, m), 1.00 (3H, t, J 7.4 Hz)

N-(2-(3-Fluorophenyl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.37 min, MH⁺ 299.0; ¹H NMR (DMSO): 10.08 (1H, s), 8.26 (1H, d,J 1.9 Hz), 8.12-8.08 (1H, m), 8.02-7.97 (1H, m), 7.79 (1H, d, J 9.0 Hz),7.75-7.69 (1H, m), 7.63 (1H, dd, J 8.8 1.9 Hz), 7.59-7.52 (1H, m),2.73-2.66 (1H, m), 1.19 (6H, d, J 6.9 Hz)

N-(2-(Benzo[d][1,3]dioxol-5-yl)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=6.14 min, MH⁺ 324.9; ¹H NMR (DMSO): 10.04 (1H, s), 8.18 (1H, d,J 1.8 Hz), 7.82 (1H, dd, J 8.2 1.8 Hz), 7.73-7.69 (2H, m), 7.58 (1H, dd,J 8.7 2.0 Hz), 7.20 (1H, d, J 8.2 Hz), 6.24 (2H, s), 2.72-2.65 (1H, m),1.19 (6H, d, J 6.9 Hz)

Ethyl 2-(4-chlorophenyl)benzo[d]oxazol-5-ylcarbamate

LCMS RT=7.14 min, MH⁺ 317.1; ¹H NMR (DMSO): 9.80 (1H, s), 8.18 (2H, d, J8.6 Hz), 7.96 (1H, d, J 1.7 Hz), 7.71-7.67 (3H, m), 7.45 (1H, dd, J 8.82.0 Hz), 4.16 (2H, q, J 7.2 Hz), 1.27 (3H, t, J 7.1 Hz)

Method 3E (Compounds II)

As Method 3C, except a flake of DMAP is added to the reaction

N-(2-(4-Chlorophenyl)benzo[d]oxazol-6-yl)isobutyramide

LCMS RT=7.07 min, MH⁺ 314.9; ¹H NMR (DMSO): 10.15 (1H, s), 8.29 (1H, d,J 1.7 Hz), 8.18 (2H, d, J 8.8 Hz), 7.73 (1H, d, J 8.7 Hz), 7.68 (2H, d,J 8.7 Hz), 7.49 (1H, dd, J 8.7 1.9 Hz), 2.64 (1H, t, J 6.8 Hz), 1.14(6H, d, J 6.8 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-6-yl)butyramide

LCMS RT=7.07 min, MH⁺ 314.9; ¹H NMR (DMSO): 10.20 (1H, s), 8.29 (1H, d,J 1.7 Hz), 8.18 (2H, d, J 8.8 Hz), 7.73 (1H, d, J 8.7 Hz), 7.68 (2H, d,J 8.7 Hz), 7.43 (1H, dd, J 8.7 1.9 Hz), 2.34 (2H, t, J 7.3 Hz),1.71-1.59 (2H, m), 0.94 (3H, t, J 7.4 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)cyclopropanecarboxamide

LCMS RT=6.69 min, MH⁺ 313.1; ¹H NMR (DMSO): 10.39 (1H, s), 8.20-8.15(3H, m), 7.74-7.68 (3H, m), 7.54 (1H, d, J 8.9 2.1 Hz), 1.84-1.76 (1H,m), 0.81-0.78 (4H, m)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)cyclobutanecarboxamide

LCMS RT=7.07 min, MH⁺ 327.0; ¹H NMR (DMSO): 9.91 (1H, s), 8.21-8.17 (3H,m), 7.73-7.67 (3H, m), 7.55 (1H, d, J 8.9 2.1 Hz), 2.33-1.81 (7H, m)

Method 3F (Compounds II)4,4,4-Trifluoro-N-(2-p-tolylbenzo[d]oxazol-5-yl)butanamide

To 4,4,4-trifluorobutanoic acid (128 mg, 0.90 mmol) in drydimethylformamide (5 mL) was added HATU (397 mg, 1.05 mmol) anddiisopropylethylamine (496 μL, 2.85 mmol). The mixture was then stirredat room temperature for 10 min. 2-p-Tolylbenzo[d]oxazol-5-amine (200 mg,0.95 mmol) was then added and the resulting mixture was stirred at roomtemperature for 16 h. Ethyl acetate was added and the organic layer waswashed once with saturated aqueous Na₂CO₃, followed by another wash withbrine. The combined organic layers were dried over anhydrous MgSO₄ andevaporated. The resulting solid was purified by column chromatographyeluting with ethyl acetate/hexanes 40:60 v/v to afford 26.7 mg (8%) ofthe title compound (LCMS RT=6.77 min, MH⁺ 348.9)

¹H NMR (DMSO): 10.28 (1H, s), 8.12 (1H, d, J 1.9 Hz), 8.08 (2H, d, J 8.2Hz), 7.72 (1H, d, J 8.8 Hz), 7.50 (1H, dd, J 8.8 2.1 Hz), 7.43 (2H, d, J8.1 Hz), 2.67-2.56 (4H, m), 2.42 (3H, s)

All compounds below were prepared following the same general method.

3-Methoxy-N-(2-p-tolylbenzo[d]oxazol-5-yl)propanamide

LCMS RT=6.03 min, MH⁺ 311.0; ¹H NMR (DMSO): 10.13 (1H, s), 8.14 (1H, d,J 2.2 Hz), 8.08 (2H, d, J 8.4 Hz), 7.70 (1H, d, J 8.9 Hz), 7.52 (1H, dd,J 8.9 2.0 Hz), 7.43 (2H, d, J 8.3 Hz), 3.65 (2H, t, J 6.2 Hz), 3.26 (3H,s), 2.61-2.56 (2H, m), 2.42 (3H, s)

Tert-butyl-3-oxo-3-(2-phenylbenzo[d]oxazol-5-ylamino)propylcarbamate

LCMS RT=6.22 min, MH⁺ 382.0; ¹H NMR (CDCl₃): 8.19-8.14 (2H, m), 7.89(2H, s), 7.50-7.42 (5H, m), 5.15-5.05 (1H, br), 3.49-3.43 (2H, m), 2.59(2H, t, J 7.6 Hz), 1.38 (9H, s)

3,3,3-Trifluoro-N-(2-p-tolylbenzo[d]oxazol-5-yl)propanamide

LCMS RT=14.01 min, MH⁺ 335.0; ¹H NMR (DMSO): 10.48 (1H, s), 8.11-8.08(3H, m), 7.75 (1H, d, J 9.0 Hz), 7.49 (1H, dd, J 8.7 2.1 Hz), 7.44 (2H,d, J 8.0 Hz), 3.55 (2H, q, J 10.9 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-3-methoxypropanamide

LCMS RT=6.32 min, MH⁺ 331.1; ¹H NMR (DMSO): 10.17 (1H, s), 8.22-8.17(3H, m), 7.74-7.68 (3H, m), 7.54 (1H, dd, J 8.9 2.1 Hz), 3.65 (2H, t, J6.1 Hz), 3.26 (3H, s), 2.59 (2H, t, J 6.1 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-3,3,3-trifluoropropanamide

LCMS RT=6.72 min, MH⁺ 354.7; ¹H NMR (DMSO): 10.52 (1H, s), 8.21 (2H, d,J 8.7 Hz), 8.14 (1H, d, J 2.0 Hz), 7.78 (1H, d, J 8.7 Hz), 7.70 (2H, d,J 8.7 Hz), 7.52 (1H, dd, J 8.8 2.1 Hz), 3.56 (2H, q, J 11.1 Hz)

N-(2-(3,4-Dichlorophenyl)benzo[d]oxazol-5-yl)-3,3,3-trifluoropropanamide

LCMS RT=7.41 min, MH⁺ 388.8; ¹H NMR (DMSO): 10.54 (1H, s), 8.36 (1H, d,J 2.0 Hz), 8.17-8.14 (2H, m), 7.90 (1H, d, J 8.4 Hz), 7.80 (1H, d, J 8.8Hz), 7.54 (1H, dd, J 8.9 2.1 Hz), 3.56 (2H, q, J 11.1 Hz)

N-(2-(2,3-Dichlorophenyl)benzo[d]oxazol-5-yl)-3,3,3-trifluoropropanamide

LCMS RT=6.76 min, MH⁺ 388.9; ¹H NMR (DMSO): 10.55 (1H, s), 8.20 (1H, d,J 1.9 Hz), 8.12 (1H, dd, J 7.9 1.6 Hz), 7.94 (1H, dd, J 8.1 1.6 Hz),7.83 (1H, d, J 8.8 Hz), 7.64-7.55 (2H, m), 3.58 (2H, q, J 11.1 Hz)

The compounds below were obtained by Method 3F, using the appropriateBoc-amino acid. Coupling was followed by deprotection of Boc group using4M HCl in dioxane for 20 min at room temperature.

(S)-N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)pyrrolidine-2-carboxamide

LCMS RT=4.54 min, MH⁺ 342.0; ¹H NMR (DMSO): 10.15 (1H, s), 8.23 (1H, d,J 1.7 Hz), 8.19 (2H, d, J 8.7 Hz), 7.74-7.63 (4H, m), 3.75-3.69 (1H, m),2.91 (2H, t, J 6.5 Hz), 2.12-2.00 (1H, m), 1.90-1.60 (3H, m)

(S)-N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-2-(methylamino)propanamide

LCMS RT=4.46 min, MH⁺ 330.1; ¹H NMR (DMSO): 8.20-8.10 (3H, m), 7.67 (2H,d, J 8.8 Hz), 7.58-7.47 (2H, m), 3.00 (1H, q, J 6.8 Hz), 2.24 (3H, s),1.16 (3H, d, J 6.8 Hz)

The compound below was obtained by Method 3F, using the appropriateFmoc-amino acid. Coupling was followed by deprotection of the Fmoc groupusing piperidine/DMF 20:80 v/v.

(S)-2-Amino-N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)propanamide

LCMS RT=4.46 min, MH⁺ 316.1; ¹H NMR (CDCl₃): 9.56 (1H, s), 8.11 (2H, d,J 8.7 Hz), 7.98 (1H, d, J 1.9 Hz), 7.55 (1H, dd, J 8.8 2.1 Hz),7.46-7.41 (3H, m), 3.60 (1H, q, J 7.0 Hz), 1.41 (3H, d, J 7.0 Hz)

Method 3G (Compounds II)

As Method 3C, except instead of the acid chloride, the correspondinganhydride was used

2,2,2-Trifluoro-N-(2-p-tolylbenzo[d]oxazol-5-yl)acetamide

LCMS RT=6.93 min, MH⁺ 321.0; ¹H NMR (DMSO): 11.46 (1H, br), 8.22 (2H, d,J 8.6 Hz), 8.15 (1H, d, J 1.9 Hz), 7.85 (1H, d, J 8.8 Hz), 7.73-7.68(3H, m)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-2,2,2-trifluoroacetamide

LCMS RT=7.12 min, MH⁺ 340.8; ¹H NMR (DMSO): 11.43 (1H, br), 8.12-8.09(3H, m), 7.82 (1H, d, J 8.8 Hz), 7.67 (1H, dd, J 8.9 2.1 Hz), 7.45 (2H,d, J 8.0 Hz)

Method 3H (Compounds II)3-Morpholino-N-(2-phenylbenzo[d]oxazol-5-yl)propanamide

To 2-phenylbenzo[d]oxazol-5-amine (75 mg, 0.36 mmol) and methyl3-morpholinopropanoate (63 μL, 0.39 mmol) in toluene (2.5 mL) was addeda 2M solution of trimethylaluminum in toluene (0.22 mL, 0.43 mmol). Theresulting solution was heated twice for 5 min at 160° C. in themicrowave. After cooling, sodium bicarbonate solution was added and theaqueous layer was extracted with ethyl acetate. The organic layer wasthen washed with brine and the combined organic layers were dried overanhydrous MgSO₄. After evaporation, the impurities were removed byfiltering through on a plug of silica eluting with ethyl acetate/hexanes50:50 v/v and the desired product was obtained by elution with methanolto afford 17.5 mg (14%) of the title compound (LCMS RT=5.54 min, MH⁺352.0)

¹H NMR (DMSO): 10.25 (1H, s), 8.22-8.15 (3H, m), 7.73 (1H, d, J 8.8 Hz),7.65-7.59 (3H, m), 7.52 (1H, dd, J 8.8 2.0 Hz), 3.60-3.57 (4H, m),2.68-2.64 (2H, m), 2.44-2.41 (4H, m)

Method 4 (Compounds III)N-(2-Phenylbenzo[d]oxazol-5-yl)propane-1-sulfonamide

To a solution of 2-phenylbenzo[d]oxazol-5-amine (100 mg, 0.48 mmol) indichloromethane (2 mL) at room temperature was added pyridine (83 μL,0.95 mmol) followed by propane-1-sulfonyl chloride (61 μL, 0.52 mmol).The resulting solution was then stirred at room temperature for 16 h.Dichloromethane was added and the organic layer was washed withsaturated aqueous copper sulfate solution. The combined organic layerswere dried over anhydrous MgSO₄ and evaporated. The resulting insolublesolid was washed with saturated aqueous NaHCO₃ to afford 37.2 mg (25%)of the title compound (LCMS RT=6.25 min, MH⁺ 317.0)

¹H NMR (DMSO): 9.89 (1H, br), 8.21-8.18 (2H, m), 7.77 (1H, d, J 8.8 Hz),7.66-7.59 (4H, m), 7.28 (1H, dd, J 8.8 2.1 Hz), 3.10-3.04 (2H, m),1.77-1.64 (2H, m), 0.94 (3H, t, J 7.5 Hz)

The compounds below were prepared following the same general method, andpurified by column chromatography eluting with ethyl acetate:hexanes30:70 v/v.

N-(2-Phenylbenzo[d]oxazol-5-yl)propane-2-sulfonamide

LCMS RT=6.16 min, MH⁺ 317.0; ¹H NMR (DMSO): 9.89 (1H, br), 8.21-8.18(2H, m), 7.76 (1H, d, J 8.8 Hz), 7.69-7.59 (4H, m), 7.30 (1H, dd, J 8.82.2 Hz), 1.26 (6H, d, J 6.9 Hz)

N-(2-Phenylbenzo[d]oxazol-5-yl)benzenesulfonamide

LCMS RT=6.43 min, MH⁺ 350.8; ¹H NMR (DMSO): 10.40 (1H, br), 8.15 (2H,dd, J 7.2 1.6 Hz), 7.77-7.74 (2H, m), 7.68-7.51 (7H, m), 7.46 (1H, d, J2.1 Hz), 7.12 (1H, dd, J 8.8 2.1 Hz)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)propane-1-sulfonamide

LCMS RT=6.53 min, MH⁺ 331.0; ¹H NMR (DMSO): 9.85 (1H, br), 8.80 (2H, d,J 7.8 Hz), 7.74 (1H, d, J 9.0 Hz), 7.60 (1H, d, J 2.0 Hz), 7.44 (2H, d,J 8.1 Hz), 7.26 (1H, dd, J 8.7 2.2 Hz), 3.09-3.04 (2H, m), 2.42 (3H, s),1.74-1.64 (2H, m), 0.94 (3H, t, J 7.6 Hz)

N-(2-p-Tolylbenzo[d]oxazol-5-yl)propane-2-sulfonamide

LCMS RT=6.58 min, MH⁺ 330.9; ¹H NMR (DMSO): 9.85 (1H, br), 8.08 (2H, d,J 8.2 Hz), 7.72 (1H, d, J 8.6 Hz), 7.62 (1H, d, J 1.8 Hz), 7.43 (2H, d,J 8.2 Hz), 7.28 (1H, dd, J 8.8 2.2 Hz), 2.60-2.57 (1H, m), 2.42 (3H, s),1.26 (6H, d, J 6.8 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)propane-1-sulfonamide

LCMS RT=6.81 min, MH⁺ 350.9; ¹H NMR (DMSO): 9.73 (1H, br), 8.20 (2H, d,J 8.7 Hz), 7.77 (1H, d, J 8.6 Hz), 7.71 (2H, d, J 8.7 Hz), 7.63 (1H, d,J 1.9 Hz), 7.29 (1H, dd, J 8.8 2.2 Hz), 3.10-3.05 (2H, m), 1.77-1.65(2H, m), 0.94 (3H, t, J 7.6 Hz)

N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)propane-2-sulfonamide

LCMS RT=6.68 min, MH⁺ 351.0; ¹H NMR (DMSO): 9.88 (1H, br), 8.19 (2H, d,J 8.7 Hz), 7.76 (1H, d, J 8.8 Hz), 7.70 (2H, d, J 8.7 Hz), 7.65 (1H, d,J 2.0 Hz), 7.32 (1H, dd, J 8.8 2.2 Hz), 3.24 (1H, t, J 6.7 Hz), 1.26(6H, d, J 6.7 Hz)

Method 5 (Compounds IV)N-(Pyridin-4-ylmethyl)-2-p-tolylbenzo[d]oxazol-5-amine

To 2-p-tolylbenzo[d]oxazol-5-amine (500 mg, 2.32 mmol) in1,2-dichloroethane (20 mL) at room temperature was added acetic acid(142 μL, 2.32 mmol) and isonicotinaldehyde (222.5 μL, 2.29 mmol) and themixture was stirred for 1 h. Sodium triacetoxyborohydride (707 mg, 3.35mmol) was then added and the mixture was stirred at room temperature for24 h. The mixture was then diluted with dichloromethane and the organiclayer was washed with saturated aqueous NaHCO₃. The combined organiclayers were dried over anhydrous MgSO₄ and evaporated. The resultingsolid was purified by column chromatography eluting with ethylacetate:hexanes 20:80 to afford 328 mg (47%) of the title compound (LCMSRT=6.27 min, MH⁺ 316.1)

¹H NMR (DMSO): 8.50 (2H, d, J 6.0 Hz), 8.00 (2H, d, J 8.1 Hz), 7.48-7.37(5H, m), 6.76-6.72 (2H, m), 6.51 (1H, t, J 6.2 Hz), 4.38 (2H, d, J 6.1Hz), 2.39 (3H, s)

All compounds below were prepared following the same general method.

N-Benzyl-2-phenylbenzo[d]oxazol-5-amine

LCMS RT=7.90 min, MH⁺ 301.0; ¹H NMR (DMSO): 9.14-8.10 (2H, m), 7.61-7.56(3H, m), 7.48-7.21 (6H, m), 6.79-6.75 (2H, m), 6.39 (1H, t, J 6.0 Hz),4.32 (2H, d, J 6.1 Hz)

N-Butyl-2-phenylbenzo[d]oxazol-5-amine

LCMS RT=8.25 min, MH⁺ 267.0; ¹H NMR (DMSO): 8.16-8.12 (2H, m), 7.61-7.58(3H, m), 7.47 (1H, d, J 8.7 Hz), 6.81 (1H, d, J 2.1 Hz), 6.72 (1H, dd, J8.8 2.3 Hz), 6.64 (1H, t, J 5.5 Hz), 3.08-3.00 (2H, m), 1.64-1.51 (2H,m), 1.49-1.35 (2H, m), 0.94 (3H, t, J 7.2 Hz)

N-Isobutyl-2-phenylbenzo[d]oxazol-5-amine

LCMS RT=8.26 min, MH⁺ 267.0; ¹H NMR (DMSO): 8.15-8.12 (2H, m), 7.62-7.51(3H, m), 7.46 (1H, d, J 8.8 Hz), 6.81 (1H, d, J 2.1 Hz), 6.74 (1H, dd, J8.8 2.3 Hz), 5.73 (1H, t, J 5.6 Hz), 2.87 (2H, t, J 6.1 Hz), 1.95-1.82(1H, m), 0.97 (6H, d, J 6.6 Hz)

N-Butyl-2-(4-chlorophenyl)benzo[d]oxazol-5-amine

LCMS RT=9.58 min, MH⁺ 301.1; ¹H NMR (DMSO): 8.14 (2H, d, J 8.7 Hz), 7.66(2H, d, J 8.7 Hz), 7.47 (1H, d, J 8.7 Hz), 6.81 (1H, d, J 2.1 Hz), 6.73(1H, dd, J 8.8 2.2 Hz), 6.67 (1H, t, J 5.7 Hz), 3.07-3.00 (2H, m),1.62-1.53 (2H, m), 1.48-1.36 (2H, m), 0.94 (3H, t, J 7.2 Hz)

2-(4-Chlorophenyl)-N-isobutylbenzo[d]oxazol-5-amine

LCMS RT=8.85 min, MH⁺ 301.0; ¹H NMR (DMSO): 8.14 (2H, d, J 8.7 Hz), 7.66(2H, d, J 8.7 Hz), 7.47 (1H, d, J 8.8 Hz), 6.80 (1H, d, J 2.0 Hz), 6.75(1H, dd, J 8.8 2.2 Hz), 5.75 (1H, t, J 5.7 Hz), 2.87 (2H, d, J 6.2 Hz),1.93-1.82 (1H, m), 0.97 (6H, d, J 6.7 Hz)

N-Benzyl-2-(4-chlorophenyl)benzo[d]oxazol-5-amine

LCMS RT=8.39 min, MH⁺ 335.0; ¹H NMR (DMSO): 8.11 (2H, d, J 8.8 Hz), 7.65(2H, d, J 8.7 Hz), 7.47 (1H, d, J 9.4 Hz), 7.42-7.21 (5H, m), 6.81-6.78(2H, m), 6.42 (1H, t, J 5.8 Hz), 4.32 (2H, d, J 6.8 Hz)

N-Butyl-2-p-tolylbenzo[d]oxazol-5-amine

LCMS RT=8.44 min, MH⁺ 281.0; ¹H NMR (DMSO): 8.02 (2H, d, J 8.2 Hz),7.46-7.38 (3H, m), 6.79 (1H, d, J 2.0 Hz), 6.69 (1H, dd, J 8.8 2.4 Hz),5.62 (1H, t, J 5.7 Hz), 3.06-3.00 (2H, m), 2.40 (3H, s), 1.62-1.53 (2H,m), 1.48-1.36 (2H, m), 0.94 (3H, t, J 7.2 Hz)

N-Isobutyl-2-p-tolylbenzo[d]oxazol-5-amine

LCMS RT=8.48 min, MH⁺ 281.0; ¹H NMR (DMSO): 8.03 (2H, d, J 8.1 Hz),7.45-7.38 (3H, m), 6.79 (1H, d, J 2.1 Hz), 6.71 (1H, dd, J 8.8 2.3 Hz),5.70 (1H, t, J 5.7 Hz), 2.86 (2H, t, J 6.3 Hz), 2.40 (3H, s), 1.95-1.81(1H, m), 0.97 (6H, d, J 6.7 Hz)

N-Benzyl-2-p-tolylbenzo[d]oxazol-5-amine

LCMS RT=7.95 min, MH⁺ 315.1; ¹H NMR (DMSO): 8.00 (2H, d, J 8.1 Hz),7.46-7.21 (8H, m), 6.77-6.73 (2H, m), 6.37 (1H, t, J 6.4 Hz), 4.32 (2H,d, J 6.0 Hz), 2.40 (3H, s)

2-(4-Chlorophenyl)-N,N-diisobutylbenzo[d]oxazol-5-amine

LCMS RT=17.03 min, MH⁺ 357.1; ¹H NMR (DMSO): 8.26 (2H, d, J 8.5 Hz),7.80 (2H, d, J 8.6 Hz), 7.67 (1H, d, J 9.0 Hz), 7.09 (1H, d, J 2.3 Hz),6.96 (1H, dd, J 9.1 2.4 Hz), 3.32 (4H, d, J 7.2 Hz), 2.20-2.10 (2H, m),1.02 (12H, d, J 6.6 Hz)

Method 6 (Compounds V) 1-Phenyl-3-(2-phenylbenzo[d]oxazol-5-yl)urea

To 2-phenylbenzo[d]oxazol-5-amine (75 mg, 0.36 mmol) in dichloromethane(2 mL) at room temperature was added phenyl isocyanate (43 μL, 0.39mmol). The solution was stirred at room temperature for 16 h. Theresulting precipitate was filtered off and washed with dichloromethaneto afford 99.9 mg (85%) of the title compound (LCMS RT=6.45 min, MH⁺330.1)

¹H NMR (DMSO): 8.85 (1H, s), 8.71 (1H, s), 8.22-8.19 (2H, m), 8.00 (1H,d, J 2.0 Hz), 7.71 (1H, d, J 8.9 Hz), 7.65-7.60 (3H, m), 7.50-7.47 (2H,m), 7.40 (1H, dd, J 8.8 2.1 Hz), 7.30 (2H, t, J 8.4 Hz), 7.02-6.95 (1H,m)

The compound below was prepared following the same general method.

1-Isopropyl-3-(2-phenylbenzo[d]oxazol-5-yl)urea

LCMS RT=5.94 min, MH⁺ 296.0; ¹H NMR (DMSO): 8.47 (1H, s), 8.20-8.16 (2H,m), 7.93 (1H, d, J 1.9 Hz), 7.64-7.59 (4H, m), 7.30 (1H, dd, J 8.8 2.1Hz), 6.03 (1H, d, J 7.5 Hz), 3.85-3.74 (1H, m), 1.12 (6H, d, J 6.5 Hz)

Method 7 (Compounds VI)N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-N-methylpropionamide

To sodium hydride (15 mg, 0.37 mmol) under nitrogen at 0° C. was slowlyadded a solution ofN-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)propionamide (100 mg, 0.33mmol) in dimethylformamide (10 mL). After 10 min at 0° C., methyl iodide(56 μL, 0.37 mmol) was added, and the solution was left warming up toroom temperature for 16 h. The mixture was then diluted with ethylacetate, and then washed three times with water. The combined organiclayers were dried over anhydrous MgSO₄ and evaporated. The resultingsolid was purified by column chromatography eluting with ethylacetate/hexanes 50:50 v/v to afford 36.4 mg (35%) of the title compound(LCMS RT=7.00 min, MH⁺ 315.0)

¹H NMR (CDCl₃): 8.13 (2H, d, J 8.6 Hz), 7.55-7.52 (2H, m), 7.46 (2H, d,J 8.6 Hz), 7.13 (1H, dd, J 8.3 2.0 Hz), 3.26 (3H, s), 2.04 (2H, q, J 7.6Hz), 1.00 (3H, t, J 7.6 Hz)

Method 7 (Compounds VIb)N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-N-methylisobutyramide

LCMS RT=7.44 min, MH⁺ 329.1; ¹H NMR (DMSO): 8.22 (2H, d, J 8.7 Hz),7.91-7.87 (2H, m), 7.72 (2H, d, J 8.6 Hz), 7.43 (1H, d, J 8.3 Hz), 3.20(3H, s), 2.46-2.42 (1H, m), 0.93 (6H, d, J 6.6 Hz)

2-(4-Chlorophenyl)-N-isobutyl-N-methylbenzo[d]oxazol-5-amine

LCMS RT=10.59 min, MH⁺ 315.1; ¹H NMR (DMSO): 8.15 (2H, d, J 8.6 Hz),7.67 (2H, d, J 8.6 Hz), 7.56 (1H, d, J 9.0 Hz), 6.96 (1H, d, J 2.5 Hz),6.84 (1H, dd, J 9.1 2.5 Hz), 3.17 (2H, d, J 7.3 Hz), 2.97 (3H, s),2.13-1.97 (1H, m), 0.90 (6H, d, J 6.7 Hz)

Method 8 (Compounds VII)N-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)-2-methylpropanethioamide

To N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)isobutyramide (50 mg, 0.16mmol) in toluene (2 mL) at 110° C. was added Lawesson's reagent (35 mg,0.09 mmol). The resulting solution was heated at 110° C. for 7 h. Aftercooling, the solution was diluted with water and extracted with ethylacetate. The combined organic layers were washed with brine, then driedover anhydrous MgSO₄ and evaporated. The resulting solid was purified bycolumn chromatography eluting with ethyl acetate/hexanes 20:80 v/v toafford 13.8 mg (26%) of the title compound (LCMS RT=7.36 min, MH⁺ 331.2)

¹H NMR (DMSO): 11.59 (1H, s), 8.37 (1H, d, J 2.0 Hz), 8.22 (2H, d, J 8.8Hz), 7.83 (1H, d, J 8.7 Hz), 7.73-7.65 (3H, m), 3.18-3.09 (1H, m), 1.25(6H, d, J 6.7 Hz)

Method 9 (Compound VIII) 2-(4-Chlorophenyl)benzo[d]oxazole-5-diazoniumtetrafluoroboric acid salt

To a solution of 2-(4-chlorophenyl)benzo[d]oxazol-5-amine (500 mg, 2.04mmol) in water (3 mL) and tetrafluoroboric acid (50% in water, 2 mL) at0° C. was added a solution of sodium nitrite (140 mg, 2.04 mmol) inwater (2 mL), dropwise over 5 min. The resulting mixture was stirred at0° C. for 15 min, and then at room temperature for 1 h. The solid wasthen filtered off, washed with dilute aqueous tetrafluoroboric acidsolution and methanol to afford 370 mg (53%) of the title compound,which was used directly without characterization.

Method 10 (Compound IX) S-2-(4-Chlorophenyl)benzo[d]oxazol-5-ylethanethioate

To a stirred solution of potassium thioacetate (130 mg, 1.13 mmol) inDMSO (2.8 mL) at room temperature was added dropwise a solution of2-(4-chlorophenyl)benzo[d]oxazole-5-diazonium tetrafluoroboric acid salt(370 mg, 1.08 mmol) in DMSO (1.4 mL). After 15 min, the mixture washeated at 70° C. for 1 h. After cooling, the mixture was diluted withwater, and then extracted several times with ethyl acetate. The combinedorganic layers were washed with brine, dried over anhydrous MgSO₄ andevaporated. The resulting solid was purified by column chromatographyeluting using a gradient (ethyl acetate/hexanes 5:95 v/v to ethylacetate/hexanes 15:85 v/v) and triturated with diethyl ether/hexanes toafford 11.3 mg (3%) of the title compound (LCMS RT=7.89 min, MH⁺ 304.2)

¹H NMR (CDCl₃): 8.24 (2H, d, J 8.7 Hz), 7.88 (1H, dd, J 1.7 0.4 Hz),7.67 (1H, dd, J 8.7 0.4 Hz), 7.57 (2H, d, J 8.8 Hz), 7.46 (1H, dd, J 8.41.7 Hz), 2.51 (3H, s)

Method 11A (Compound X)5-(Ethylsulfonyl)-2-(5-methylthiophen-2-yl)benzo[d]oxazole

To a stirred solution of 2-amino-4-(ethylsulfonyl)phenol (452.7 mg, 2.25mmol) in ethanol (17 mL) was added 5-methyl-2-thiophenecarboxaldehyde(242 μL, 2.25 mmol). The mixture was heated at 70° C. for 70 min. Aftercooling, a small amount of precipitate was formed. After filtration andevaporation of the filtrate, the resulting product was dissolved inacetonitrile (9.8 mL) and lead tetraacetate (887 mg, 2 mmol) was added.The resulting mixture was heated at 100° C. for 5 min. After cooling,the reaction mixture was filtered off, and the filtrate evaporated invacuo. The resulting mixture was purified by column chromatographyeluting with ethyl acetate/hexanes 20:80 v/v, and then purified byreverse phase HPLC to afford 2.2 mg (0.3%) of the title product (LCMSRT=6.41 min, MH⁺ 308.1)

¹H NMR (DMSO): 8.22 (1H, dd, J 1.8 0.5 Hz), 8.02 (1H, dd, J 8.6 0.5 Hz),7.92-7.88 (2H, m), 7.08 (1H, dd, J 3.7 1.0 Hz), 3.37 (2H, q, J 7.3 Hz),2.60 (3H, d, J 0.6 Hz), 1.12 (3H, t, J 7.4 Hz)

Method 11B (Compounds X)

As for Method 11A, but iodosobenzene diacetate was used instead of leadtetraacetate

5-(Ethylsulfonyl)-2-(thiophen-2-yl)benzo[d]oxazole

LCMS RT=6.08 min, MH⁺ 294.1; ¹H NMR (DMSO): 8.26 (1H, d, J 1.7 Hz),8.08-8.04 (3H, m), 7.93 (1H, dd, J 8.5 1.8 Hz), 7.36 (1H, dd, J 4.9 3.8Hz), 3.38 (2H, q, J 7.3 Hz), 1.13 (3H, t, J 7.4 Hz)

5-(Ethylsulfonyl)-2-(3-methylthiophen-2-yl)benzo[d]oxazole

LCMS RT=6.45 min, MH⁺ 308.1; ¹H NMR (DMSO): 8.02 (1H, d, J 1.8 0.5 Hz),7.81 (1H, dd, J 8.5 0.5 Hz), 7.69-7.66 (2H, m), 6.98 (1H, dd, J 5.0 0.4Hz), 3.15 (2H, q, J 7.3 Hz), 2.47 (3H, s), 0.88 (3H, t, J 7.4 Hz)

5-(Ethylsulfonyl)-2-(5-methylfuran-2-yl)benzo[d]oxazole

LCMS RT=5.53 min, MH⁺ 292.1; ¹H NMR (DMSO): 8.00 (1H, d, J 1.8 0.6 Hz),7.81 (1H, d, J 6.6 Hz), 7.69 (1H, dd, J 8.6 1.9 Hz), 7.26 (1H, d, J 3.7Hz), 6.31-6.27 (1H, m), 3.18-3.14 (2H, m), 2.24 (3H, s), 0.90 (3H, t, J7.4 Hz)

5-(Ethylsulfonyl)-2-(4-methylthiophen-2-yl)benzo[d]oxazole

LCMS RT=6.40 min, MH⁺ 616.9; ¹H NMR (DMSO): 8.24 (1H, d, J 1.8 0.5 Hz),8.03 (1H, dd, J 8.6 0.5 Hz), 7.94-7.89 (2H, m), 7.65 (1H, t, J 1.2 Hz),3.42-3.36 (2H, m), 2.32 (3H, d, J 0.6 Hz), 1.12 (3H, t, J 7.5 Hz)

Method 12 (Compounds XI) N-Butyl-2-p-tolylbenzo[d]oxazole-5-carboxamide

To 2-p-tolylbenzo[d]oxazole-5-carboxylic acid (100 mg, 0.39 mmol) in drydimethylformamide (10 mL) was added HATU (165 mg, 0.44 mmol) anddiisopropylethylamine (206 μL, 1.18 mmol). The mixture was then stirredat room temperature for 10 min. Butan-1-amine (43 μL, 0.44 mmol) wasthen added and the resulting mixture was stirred at room temperature for16 h. Ethyl acetate was added and the organic layer was washed threetimes with water. The combined organic layers were dried over anhydrousMgSO₄ and evaporated. The resulting solid was purified by columnchromatography eluting with ethyl acetate/hexanes 40:60 v/v to afford 26mg (11%) of the title compound (LCMS RT=6.81 min, MH⁺ 309.1)

¹H NMR (CDCl₃): 8.22-8.15 (3H, m), 7.89 (1H, dd, J 8.1 1.1 Hz), 7.67(1H, d, J 8.3 Hz), 7.40 (2H, d, J 7.5 Hz), 6.17 (1H, br), 3.59-3.52 (2H,m), 2.51 (3H, s), 1.72-1.64 (2H, m), 1.54-1.46 (2H, m), 1.03 (3H, t, J7.3 Hz)

All compounds below were prepared following the same general method.

N-Propyl-2-p-tolylbenzo[d]oxazole-5-carboxamide

LCMS RT=6.42 min, MH⁺ 295.1; ¹H NMR (CDCl₃): 8.08 (2H, d, J 8.2 Hz),8.04 (1H, d, J 1.4 Hz), 7.77 (1H, dd, J 8.5 1.7 Hz), 7.54 (1H, d, J 8.6Hz), 7.28 (2H, d, J 7.9 Hz), 6.07 (1H, br), 3.44-3.37 (2H, m), 2.39 (3H,s), 1.65-1.55 (2H, m), 0.95 (3H, t, J 7.5 Hz)

N-Isopropyl-2-p-tolylbenzo[d]oxazole-5-carboxamide

LCMS RT=6.38 min, MH⁺ 295.1; ¹H NMR (CDCl₃): 8.20 (2H, d, J 8.2 Hz),8.15 (1H, d, J 1.4 Hz), 7.87 (1H, dd, J 8.5 1.8 Hz), 7.65 (1H, d, J 8.5Hz), 7.40 (2H, d, J 8.0 Hz), 6.00 (1H, br), 4.43-4.31 (1H, m), 2.51 (3H,s), 1.35 (6H, d, J 6.6 Hz)

2-p-Tolylbenzo[d]oxazole-5-carboxamide

LCMS RT=5.61 min, MH⁺ 253.0; ¹H NMR (DMSO): 8.30 (1H, d, J 1.2 Hz), 8.12(2H, d, J 8.2 Hz), 7.98 (1H, dd, J 8.5 1.7 Hz), 7.81 (1H, d, J 8.5 Hz),7.45 (2H, d, J 8.0 Hz), 2.44 (3H, s)

2-(4-Chlorophenyl)-N-isopropylbenzo[d]oxazole-5-carboxamide

LCMS RT=6.68 min, MH⁺ 315.5; ¹H NMR (DMSO): 8.36-8.31 (2H, m), 8.23 (2H,d, J=8.7 Hz), 7.98 (1H, dd, J 8.5 1.7 Hz), 7.87 (1H, d, J 8.5 Hz), 7.72(2H, d, J 8.7 Hz), 4.19-4.08 (1H, m), 1.21 (6H, d, J 6.6 Hz)

2-(4-Chlorophenyl)benzo[d]oxazole-5-carboxamide

LCMS RT=5.81 min, MH⁺ 273.2; ¹H NMR (DMSO): 8.11 (1H, s), 8.01 (2H, d, J8.3 Hz), 7.89 (1H, br), 7.78 (1H, d, J 8.6 Hz), 7.64 (1H, d, J 8.6 Hz),7.49 (2H, d, J 8.3 Hz), 7.25 (1H, br)

Method 8 (Compounds iso-VI)

2-(4-Chlorophenyl)-N-methylbenzo[d]oxazole-5-carboxamide

LCMS RT=6.09 min, MH⁺ 286.9; ¹H NMR (DMSO): 8.57 (1H, br), 8.28 (1H, d,J 1.2 Hz), 8.23 (2H, d, J 8.7 Hz), 7.96 (1H, dd, J 8.6 1.7 Hz), 7.87(1H, d, J 8.6 Hz), 7.72 (2H, d, J 8.6 Hz), 2.83 (3H, d, J 4.5 Hz)

2-(4-Chlorophenyl)-N-isopropyl-N-methylbenzo[d]oxazole-5-carboxamide

LCMS RT=6.90 min, MH⁺ 329.0; ¹H NMR (DMSO): 8.23 (2H, d, J 8.6 Hz),7.88-7.81 (2H, m), 7.72 (2H, d, J 8.7 Hz), 7.44 (1H, d, J 8.2 Hz),2.88-2.78 (3H, m), 1.18-1.12 (6H, m)

Method 7 (Compounds iso-VII)

2-(4-Chlorophenyl)-N-isopropylbenzo[d]oxazole-5-carbothioamide

LCMS RT=7.37 min, MH⁺ 331.0; ¹H NMR (DMSO): 10.18 (1H, d, J 7.3 Hz),8.23 (2H, d, J 8.8 Hz), 8.11 (1H, dd, J 1.7 0.5 Hz), 7.88 (1H, dd, J 8.61.8 Hz), 7.83 (1H, dd, J 8.8

Method 13 (Compounds XII) 5-(4-Methoxyphenyl)-2-p-tolylbenzo[d]oxazole

To a solution of 5-bromo-2-p-tolylbenzo[d]oxazole (146.1 mg, 0.50 mmol)in dioxane (1.5 mL) was added water (0.5 mL), 4-methoxyphenylboronicacid (114 mg, 0.75 mmol), potassium carbonate (138 mg, 1.00 mmol) andtetrakis(triphenylphosphine)palladium(0) (3 mg). The resultingsuspension was heated in the microwave at 150° C. for 15 min. Aftercooling, the reaction was diluted with water and extracted with ethylacetate. The combined organic layers were dried over anhydrous MgSO₄ andevaporated. The resulting solid was purified by column chromatographyeluting with ethyl acetate/hexanes 1:99 v/v to afford 60 mg (38%) of thetitle compound (LCMS RT=9.18 min, MH⁺ 316.1)

¹H NMR (DMSO): 8.12 (2H, d, J 8.2 Hz), 7.99 (1H, d, J 1.5 Hz), 7.82 (1H,d, J 8.5 Hz), 7.71-7.64 (3H, m), 7.45 (2H, d, J 8.0 Hz), 7.06 (2H, d, J8.8 Hz), 3.82 (3H, s), 2.43 (3H, s)

All compounds below were prepared following the same general method.

N-(4-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)phenyl)acetamide

LCMS RT=7.51 min, MH⁺ 362.8; ¹H NMR (DMSO): 10.04 (1H, s), 8.23 (2H, d,J 8.5 Hz), 8.05 (1H, d, J 1.6 Hz), 7.86 (1H, d, J 8.5 Hz), 7.73-7.69(7H, m), 2.09 (3H, s)

2-(4-Chlorophenyl)-5-(4-(ethylsulfonyl)phenyl)benzo[d]oxazole

LCMS RT=8.31 min, MH⁺ 397.8; ¹H NMR (DMSO): 8.27-8.23 (3H, m), 8.09-7.94(5H, m), 7.85 (1H, dd, J 8.6 1.8 Hz), 7.73 (2H, d, J 8.7 Hz), 3.39-3.34(2H, m), 1.16 (3H, t, J=7.5 Hz)

Methyl 4-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)benzoate

LCMS RT=9.34 min, MH⁺ 363.9; ¹H NMR (DMSO): 8.25 (2H, d, J 8.7 Hz), 8.20(1H, d, J 1.3 Hz), 8.08 (2H, d, J 8.6 Hz), 7.95-7.91 (3H, m), 7.83 (1H,dd, J 8.6 1.8 Hz), 7.73 (2H, d, J 8.7 Hz), 3.90 (3H, s)

N-(3-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)phenyl)acetamide

LCMS RT=7.40 min, MH⁺ 363.0; ¹H NMR (DMSO): 10.05 (1H, s), 8.25 (2H, d,J 8.7 Hz), 8.00 (1H, d, J 1.4 Hz), 7.98-7.95 (1H, m), 7.90 (1H, d, J 8.5Hz), 7.72 (2H, d, J 8.8 Hz), 7.67 (1H, dd, J 8.5 1.8 Hz), 7.60-7.57 (1H,m), 7.42-7.40 (2H, m), 2.09 (3H, s)

2-(4-Chlorophenyl)-5-(4-morpholinophenyl)benzo[d]oxazole

LCMS RT=17.49 min, MH⁺ 391.0; ¹H NMR (DMSO): 8.23 (2H, d, J 8.9 Hz),8.00 (1H, d, J 1.4 Hz), 7.83 (1H, d, J 8.6 Hz), 7.74-7.67 (3H, m), 7.64(2H, d, J 8.9 Hz), 7.06 (2H, d, J 8.9 Hz), 3.79-3.75 (4H, m), 3.19-3.15(4H, m)

2-(4-Chlorophenyl)-5-(3-(ethylthio)phenyl)benzo[d]oxazole

LCMS RT=10.82 min, MH⁺ 365.7; ¹H NMR (DMSO): 8.25 (2H, d, J 8.7 Hz),8.11 (1H, d, J 1.4 Hz), 7.89 (1H, d, J 8.6 Hz), 7.77-7.70 (3H, m), 7.62(1H, t, J 1.7 Hz), 7.55 (1H, dt, J 7.6 1.2 Hz), 7.44 (1H, t, J 7.6 Hz),7.35-7.32 (1H, m), 3.09 (2H, q, J 7.3 Hz), 1.29 (3H, t, J 7.4 Hz)

N-(2-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)phenyl)acetamide

LCMS RT=6.84 min, MH⁺ 363.0; ¹H NMR (DMSO): 9.29 (1H, s), 8.24 (2H, d, J8.6 Hz), 7.86 (1H, d, J 8.4 Hz), 7.78-7.76 (1H, m), 7.72 (2H, d, J 8.5Hz), 7.53-7.29 (5H, m), 1.87 (3H, s)

2-(4-Chlorophenyl)-5-(4-methoxypyridin-3-yl)benzo[d]oxazole

LCMS RT=7.46 min, MH⁺ 337.0; ¹H NMR (DMSO): 8.49 (1H, d, J 5.8 Hz), 8.45(1H, s), 8.24 (2H, d, J 8.9 Hz), 7.95 (1H, d, J 1.7 0.5 Hz), 7.87 (1H,dd, J 8.5 0.6 Hz), 7.72 (2H, d, J 8.8 Hz), 7.58 (1H, dd, J 8.5 1.7 Hz),7.21 (1H, d, J 5.8 Hz), 3.89 (3H, s)

2-(4-Chlorophenyl)-5-(6-methoxypyridin-3-yl)benzo[d]oxazole

LCMS RT=8.83 min, MH⁺ 337.0; ¹H NMR (DMSO): 8.57 (1H, dd, J 2.6 0.6 Hz),8.24 (2H, d, J 8.8 Hz), 8.13-8.10 (2H, m), 7.89 (1H, dd, J 8.6 0.5 Hz),7.75-7.70 (3H, m), 6.95 (1H, dd, J 8.6 0.6 Hz), 3.92 (3H, s)

3-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)benzoic acid

LCMS RT=4.62 min, MH⁺ 350.1; ¹H NMR (DMSO): 8.27-8.23 (3H, m), 8.12 (1H,d, J=1.4 Hz), 8.03-7.95 (2H, m), 7.91 (1H, d, J 8.7 Hz), 7.78 (1H, dd, J8.5 1.8 Hz), 7.72 (2H, d, J 8.8 Hz), 7.64 (1H, t, J 7.7 Hz)

2-(4-Chlorophenyl)-5-(6-chloropyridin-3-yl)benzo[d]oxazole

LCMS RT=8.59 min, MH⁺ 340.9; ¹H NMR (DMSO): 8.33 (1H, d, J 2.2 Hz),8.28-8.23 (4H, m), 7.95 (1H, d, J 8.6 Hz), 7.83 (1H, dd, J 8.5 1.8 Hz),7.73 (2H, d, J 8.7 Hz), 7.65 (1H, d, J 8.4 Hz)

2-(4-Chlorophenyl)-5-(6-fluoropyridin-3-yl)benzo[d]oxazole

LCMS RT=8.05 min, MH⁺ 325.0; ¹H NMR (DMSO): 8.65 (1H, d, J 2.7 Hz), 8.39(1H, td, J 8.2 2.7 Hz), 8.25 (2H, d, J 8.7 Hz), 8.20 (1H, dd, J 1.8 0.5Hz), 7.94 (1H, dd, J 8.6 0.6 Hz), 7.80 (1H, dd, J 8.6 1.9 Hz), 7.73 (2H,d, J 8.7 Hz), 7.33 (1H, dd, J 8.6 3.0 Hz)

2-(4-Chlorophenyl)-5-(6-morpholinopyridin-3-yl)benzo[d]oxazole

LCMS RT=8.46 min, MH⁺ 391.8; ¹H NMR (DMSO): 8.55 (1H, d, J 2.4 Hz), 8.23(2H, d, J 8.7 Hz), 8.06 (1H, d, J 1.4 Hz), 7.98 (1H, dd, J 8.9 2.6 Hz),7.86 (1H, d, J 8.8 Hz), 7.73-7.69 (3H, m), 6.96 (1H, d, J 8.9 Hz),3.75-3.71 (4H, m), 3.53-3.49 (4H, m)

2-(4-Chlorophenyl)-5-(6-methoxypyridin-2-yl)benzo[d]oxazole

LCMS RT=9.84 min, MH⁺ 337.1; ¹H NMR (DMSO): 8.54 (1H, d, J 1.6 Hz),8.26-8.23 (3H, m), 7.91 (1H, d, J 8.7 Hz), 7.82 (1H, t, J 7.9 Hz),7.74-7.68 (3H, m), 6.81 (1H, d, J=8.1 Hz), 4.00 (3H, s)

3-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)aniline

LCMS RT=7.78 min, MH⁺ 321.1; ¹H NMR (DMSO): 8.24 (2H, d, J 8.7 Hz), 7.73(1H, dd, J 1.8 0.4 Hz), 7.85 (1H, d, J 8.5 Hz), 7.72 (2H, d, J 8.8 Hz),7.63 (1H, dd, J 8.6 1.8 Hz), 7.13 (1H, t, J 7.8 Hz), 6.90 (1H, t, J 1.9Hz), 6.87-6.82 (1H, m), 6.62-6.57 (1H, m), 5.19 (2H, s)

4-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)aniline

LCMS RT=7.77 min, MH⁺ 321.1; ¹H NMR (DMSO): 8.22 (2H, d, J 8.7 Hz), 7.91(1H, d, J 1.5 Hz), 7.78 (1H, d, J 8.6 Hz), 7.71 (2H, d, J 8.6 Hz), 7.61(1H, dd, J 8.6 1.8 Hz), 7.43 (2H, d, J 8.6 Hz), 6.67 (2H, d, J 8.6 Hz),5.26 (2H, s)

5-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)pyridin-2-amine

LCMS RT=7.12 min, MH⁺ 322.1; ¹H NMR (DMSO): 8.32 (1H, d, J 2.2 Hz), 8.23(2H, d, J 8.7 Hz), 7.98 (1H, d, J 1.4 Hz), 7.84-7.77 (2H, m), 7.72 (2H,d, J 8.7 Hz), 7.64 (1H, dd, J 8.5 1.8 Hz), 6.56 (1H, d, J 8.6 Hz), 6.09(2H, s)

4-(5-(4-Chlorophenyl)benzo[d]oxazol-2-yl)aniline

LCMS RT=7.73 min, MH⁺ 320.9; ¹H NMR (DMSO): 7.94 (1H, d, J 1.5 Hz), 7.89(2H, d, J 8.6 Hz), 7.78-7.74 (3H, m), 7.60 (1H, dd, J 8.6 1.8 Hz), 7.53(2H, d, J 8.6 Hz), 6.71 (2H, d, J 8.7 Hz), 6.04 (2H, s)

Method 13a (Compound XIIa)

N-(5-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)pyridin-2-yl)acetamide

To 5-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)pyridin-2-amine (96.5 mg,0.30 mmol) in dry pyridine (3 mL) at room temperature was added acetylchloride (26 μL, 0.36 mmol), and stirred at 80° C. for 40 h. Aftercooling, the mixture was poured into water to give a precipitate, whichwas filtered off. The resulting solid was purified by columnchromatography eluting with ethyl acetate/hexanes 20:80 v/v to afford 45mg (41%) of the title compound.

¹H NMR (DMSO): 10.61 (1H, s), 8.73-8.71 (1H, m), 8.24 (2H, d, J 8.6 Hz),8.18-8.16 (3H, m), 7.91 (1H, d, J 8.5 Hz), 7.79 (1H, dd, J 8.6 1.8 Hz),7.73 (2H, d, J 8.6 Hz), 2.13 (3H, s)

Method 13b (Compound XIIb) Methyl ethylphosphinate

In accordance with well known procedures (see Xu, Y. et al., Synthesis,1984, 778-780.), a solution of methanol (2.70 mL, 66.75 mmol) andtriethylamine (4.23 mL, 30.35 mmol) in diethyl ether (1 5 mL) was addeddropwise at 0° C. to a solution of ethyl dichlorophosphine (3.15 mL,30.35 mmol) in diethyl ether (30 mL). After the addition was complete,the resulting slurry was refluxed for 1 h. After cooling at 0° C., theprecipitated solid was filtered off and washed with diethyl ether. Thefiltrate was then concentrated to afford a colourless oil, which wasused without any purification in the next step.

Methyl 2-(4-chlorophenyl)benzo[d]oxazol-5-yl(ethyl)phosphinate

To 5-bromo-2-p-tolylbenzo[d]oxazole (519.7 mg, 1.68 mmol) and methylethylphosphinate (276.9 mg, 2.02 mmol) in anhydrous toluene (10 mL) wasadded tetrakis(triphenylphosphine)palladium(0) (101.6 mg) andtriethylamine (7.5 mL, 5.4 mmol). The resulting suspension was refluxedunder nitrogen for 18 h. After cooling, ethyl acetate was added, and theorganic layer was washed with water. The combined organic layers weredried over anhydrous MgSO₄ and evaporated. The resulting solid waspurified by column chromatography eluting using a gradient (startingwith hexanes to ethyl acetate and then methanol/ethyl acetate 5:95 v/v)and then purified by reverse phase HPLC to afford 10.4 mg (2%) of thetitle product (LCMS RT=6.32 min, MH⁺ 336.1)

¹H NMR (DMSO): 8.24 (2H, d, J 8.7 Hz), 8.18-8.13 (1H, m), 8.00 (1H, ddd,J 8.5 2.4 0.6 Hz), 7.81 (1H, ddd, J 10.9 8.2 1.4 Hz), 7.73 (2H, d, J 8.7Hz), 3.54 (3H, d, J 10.9 Hz), 2.09-1.94 (2H, m), 1.04-0.91 (3H, m)

Method 14 (Compounds XIII)N-(4-(5-Chlorobenzo[d]oxazol-2-yl)phenyl)acetamide

To a solution of 4-(5-chlorobenzo[d]oxazol-2-yl)aniline (122.3 mg, 0.50mmol) in pyridine (3 mL) at room temperature was added acetyl chloride(39 μL, 0.55 mmol). The resulting mixture was stirred at roomtemperature for 16 h. The solution was then poured into water, and theresulting precipitate collected by filtration. The solid was washed withdiluted hydrochloric acid solution, followed by diluted sodium hydroxidesolution, and then by water to afford 120 mg (84%) of the title compound(LCMS RT=6.38 min, MH⁺ 287.0)

¹H NMR (DMSO): 10.33 (1H, s), 8.14 (2H, d, J 8.7 Hz), 7.88-7.80 (4H, m),7.45 (1H, dd, J 8.7 2.1 Hz), 2.11 (3H, s)

All compounds below were prepared following the same general method.N-(4-(5-Chlorobenzo[d]oxazol-2-yl)phenyl)isobutyramide

LCMS RT=7.03 min, MH⁺ 315.1; ¹H NMR (DMSO): 10.22 (1H, s), 8.14 (2H, d,J 8.7 Hz), 7.88-7.79 (4H, m), 7.45 (1H, dd, J 8.7 2.1 Hz), 2.70-2.61(1H, m), 1.13 (6H, d, J 6.8 Hz)

N-(4-(5-Chlorobenzo[d]oxazol-2-yl)phenyl)thiophene-2-carboxamide

LCMS RT=7.44 min, MH⁺ 355.0; ¹H NMR (DMSO): 10.57 (1H, s), 8.21 (2H, d,J 8.9 Hz), 8.09 (1H, dd, J 3.8 1.1 Hz), 8.02 (2H, d, J 8.9 Hz),7.93-7.90 (2H, m), 7.82 (1H, d, J=8.6 Hz), 7.46 (1H, dd, J 8.6 2.1 Hz),7.27 (1H, dd, J 4.9 3.8 Hz)

N-(4-(6-Chlorobenzo[d]oxazol-2-yl)phenyl)acetamide

LCMS RT=6.37 min, MH⁺ 287.0; ¹H NMR (DMSO): 10.32 (1H, s), 8.13 (2H, d,J 8.8 Hz), 7.96 (1H, d, J 1.8 Hz), 7.84-7.77 (3H, m), 7.45 (1H, dd, J8.4 1.9 Hz), 2.11 (3H, s)

N-(4-(6-Chlorobenzo[d]oxazol-2-yl)phenyl)isobutyramide

LCMS RT=7.18 min, MH⁺ 315.1; ¹H NMR (DMSO): 10.22 (1H, s), 8.12 (2H, d,J 8.8 Hz), 7.96 (1H, d, J 1.8 Hz), 7.86 (2H, d, J 8.9 Hz), 7.79 (1H, d,J 8.5 Hz), 7.45 (1H, dd, J 8.5 2.0 Hz), 2.70-2.61 (1H, m), 1.13 (6H, d,J 6.9 Hz)

N-(4-(6-Chlorobenzo[d]oxazol-2-yl)phenyl)thiophene-2-carboxamide

LCMS RT=7.61 min, MH⁺ 354.9; ¹H NMR (DMSO): 10.57 (1H, s), 8.19 (2H, d,J 8.9 Hz), 8.09 (1H, dd, J 3.7 1.0 Hz), 8.01 (2H, d, J 8.9 Hz), 7.98(1H, d, J 1.8 Hz), 7.92 (1H, dd, J 5.0 1.0 Hz), 7.81 (1H, d, J 8.5 Hz),7.46 (1H, dd, J 8.5 2.0 Hz), 7.26 (1H, dd, J 5.0 3.8 Hz)

N-(4-(5-Bromobenzo[d]oxazol-2-yl)phenyl)acetamide

¹H NMR (DMSO): 10.35 (1H, s), 8.14 (2H, d, J 8.8 Hz), 8.01 (1H, d, J 1.8Hz), 7.83 (2H, d, J 8.7 Hz), 7.76 (1H, d, J 8.6 Hz), 7.57 (1H, dd, J 8.62.0 Hz), 2.11 (3H, s)

N-(4-(5-(4-Chlorophenyl)benzo[d]oxazol-2-yl)phenyl)acetamide

LCMS RT=7.53 min, MH⁺ 363.0; ¹H NMR (DMSO): 10.34 (1H, s), 8.17 (2H, d,J 8.7 Hz), 8.06-8.04 (1H, m), 7.87-7.82 (3H, m), 7.78 (2H, d, J 8.5 Hz),7.72-7.67 (1H, m), 7.55 (2H, d, J 8.6 Hz), 2.12 (3H, s)

N-(4-(5,6-Dimethylbenzo[d]oxazol-2-yl)-3-hydroxyphenyl)acetamide

LCMS RT=7.22 min, MH⁺ 297.2; ¹H NMR (DMSO): 11.24 (1H, br), 10.24 (1H,s), 7.91 (1H, d, J 8.6 Hz), 7.59 (2H, d, J 6.4 Hz), 7.51 (1H, d, J 1.9Hz), 7.22 (1H, dd, J 8.7 2.0 Hz), 2.37 (3H, s), 2.34 (3H, s), 2.09 (3H,s)

Method 15 (Compounds XIV)1-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)ethanol

To a solution of 1-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)ethanone (150mg, 0.55 mmol) in tetrahydrofuran at 0° C. was added sodium borohydride(52 mg, 1.38 mmol). The resulting mixture was stirred at roomtemperature for 16 h. The reaction was then quenched at 0° C. with 1Mhydrochloric acid solution and extracted three times with ethyl acetate.The combined organic layers were dried over anhydrous MgSO₄ andevaporated. The resulting solid was purified by column chromatographyeluting using a gradient (ethyl acetate/hexanes 1:3 v/v to ethylacetate/hexanes 1:2 v/v) to afford 81.7 mg (54%) of the title compound.(LCMS RT=6.47 min, MH⁺ 274.0)

¹H NMR (DMSO): 8.20 (2H, d, J 8.7 Hz), 7.76-7.68 (4H, m), 7.44 (1H, dd,J 8.6 1.6 Hz), 5.31 (1H, d, J 4.3 Hz), 4.92-4.83 (1H, m), 1.38 (3H, d, J6.4 Hz)

2-(3′,4′-Dichlorophenyl)-5-(1′-hydroxyethyl)-benzoxazole

LCMS RT=7.18 min, MH⁺ 308.1; ¹H NMR (DMSO): 8.36 (1H, d, J 2.0 Hz), 8.16(1H, dd, J 8.5 2.0 Hz), 7.90 (1H, d, J 8.4 Hz), 7.78-7.77 (1H, m), 7.74(1H, d, J 8.4 Hz), 7.47 (1H, dd, J 8.6 1.7 Hz), 5.32 (1H, d, J 4.3 Hz),4.93-4.84 (1H, m), 1.39 (3H, d, J 6.4 Hz)

5-Nitrobenzo[d]oxazole-2(3H)-thione

In accordance with well known procedures, (see Batista-Parra, A. et al.Heterocycles, 2003, 60, 1367), a suspension of 2-amino-4-nitrophenol(1.54 g, 10 mmol) and potassium O-ethyl carbonodithioate (1.68 g, 10.5mmol) in dry pyridine (10 mL) was stirred at 120° C. for 6 h, and thenat room temperature for 16 h. The solution was poured into water andaqueous hydrochloric acid was added. The resulting precipitate wascollected by filtration, washed with dilute aqueous hydrochloric acid,followed by water and then dried in the vacuum oven to afford 3.3 g(84%) of the title compound.

¹H NMR (DMSO): 8.18 (1H, dd, J 8.9 2.4 Hz), 7.94 (1H, dd, J 2.4 0.4 Hz),7.73 (1H, dd, J 8.9 0.4 Hz)

Method 16 (Compound XV) 2-Morpholino-5-nitrobenzo[d]oxazole

5-nitrobenzo[d]oxazole-2(3H)-thione (98.1 mg, 0.5 mmol) and morpholine(66 μL, 0.75 mmol) in tetrahydrofuran (3 mL) were heated at 150° C. for15 min in the microwave. After cooling, the mixture was poured intowater and extracted with ethyl acetate. The organic layer was washedwith brine, dried over anhydrous MgSO₄ and absorbed on silica.Purification by column chromatography, eluting with ethylacetate/hexanes 25:75 v/v affords 115 mg (92%) of the title compound.

¹H NMR (DMSO): 8.10 (1H, d, J 2.3 Hz), 8.00 (1H, dd, J 8.8 2.4 Hz), 7.66(1H, d, J 8.8 Hz), 3.76-3.72 (4H, m), 3.67-3.64 (4H, m)

Method 17a (Compound XVI) 2-Morpholinobenzo[d]oxazol-5-amine

A solution of 2-morpholino-5-nitrobenzo[d]oxazole (130 mg, 0.52 mmol) inethanol/water 1:1 v/v (10 mL) was treated with sodium dithionite (182mg, 1.04 mmol) at room temperature and then refluxed for 16 h. Aftercooling, the mixture was diluted with water and extracted with ethylacetate. The organic layer was dried over anhydrous MgSO₄ and evaporatedto afford 35 mg (30%) of the title compound.

¹H NMR (DMSO): 7.03 (1H, d, J 8.5 Hz), 6.50 (1H, d, J 2.1 Hz), 6.25 (1H,dd, J 8.4 2.2 Hz), 4.80 (2H, s), 3.71-3.68 (4H, m), 3.53-3.50 (4H, m)

Method 17b (Compound XVI)N-2-(4-Chlorobenzyl)benzo[d]oxazole-2,5-diamine

To a suspension of N-(4-chlorobenzyl)-5-nitrobenzo[d]oxazol-2-amine (150mg, 0.50 mmol) in ethanol/water 1:1 v/v (10 mL) at 90° C. was addedammonium chloride (53 mg, 1.0 mmol), followed by iron powder (140 mg,2.5 mmol). The resulting mixture was stirred for 4 h at 90° C. Aftercooling, ethyl acetate was added and the solution was passed through apad of Celite®. The organic layer was then washed with brine, dried overanhydrous MgSO₄ and evaporated. The resulting solid was purified bycolumn chromatography eluting with ethyl acetate/hexanes 50:50 v/v toafford 60 mg (44%) of the title compound (LCMS RT=5.60 min, MH⁺ 274.0)

¹H NMR (DMSO): 8.20 (1H, t, J 6.2 Hz), 7.42-7.36 (4H, m), 6.97 (1H, d, J8.4 Hz), 6.45 (1H, d, J 2.1 Hz), 6.20 (1H, dd, J 8.4 2.2 Hz), 4.72 (2H,s), 4.46 (2H, d, J 6.2 Hz)

Method 18 (Compound XVII) 2-(4-Chlorobenzylthio)-5-nitrobenzo[d]oxazole

To a suspension of 5-nitrobenzo[d]oxazole-2(3H)-thione (196.2 mg, 1.0mmol) in chloroform (10 mL) was added triethylamine (278 μL, 2 mmol)followed by 1-(bromomethyl)-4-chlorobenzene (226 mg, 1.1 mmol). Thereaction was stirred at 60° C. for 2 h. After cooling, the reaction wasdiluted with ethyl acetate, washed with dilute aqueous hydrochloricsolution and brine. The combined organic layers were dried overanhydrous MgSO₄ and evaporated. The resulting solid was purified bycolumn chromatography eluting with ethyl acetate/hexanes 1:10 v/v toafford 250 mg (78%) of the title compound (LCMS RT=7.64 min)

¹H NMR (DMSO): 8.52 (1H, d, J 2.3 Hz), 8.27 (1H, dd, J 8.9 2.3 Hz), 7.92(1H, d, J 9.0 Hz), 7.58 (2H, d, J 8.5 Hz), 7.42 (2H, d, J 8.5 Hz), 4.67(2H, s)

Method 19 (Compound XVIII) 2-(4-Chlorobenzylthio)benzo[d]oxazol-5-amine

To a suspension of 2-(4-chlorobenzylthio)-5-nitrobenzo[d]oxazole (220mg, 0.70 mmol) in ethanol/water (5 mL/5 mL) at 90° C. was added ammoniumchloride (75 mg, 1.4 mmol), followed by iron powder (192 mg, 3.44 mmol).The resulting mixture was stirred for 4 h at 90° C. After cooling, ethylacetate was added and the solution was passed through a pad of Celite®.The organic layer was then washed with brine, dried over anhydrous MgSO₄and evaporated to afford 190 mg (94%) of the title compound (LCMSRT=6.54 min, MH⁺ 290.9)

¹H NMR (DMSO): 7.52 (2H, d, J 8.7 Hz), 7.40 (2H, d, J 8.5 Hz), 7.26 (1H,d, J 8.7 Hz), 6.74 (1H, d, J 1.9 Hz), 6.54 (1H, dd, J 8.7 2.2 Hz), 5.06(2H, s), 4.55 (2H, s)

Method 20 (Compounds XIX)N-(2-(4-Chlorobenzylthio)benzo[d]oxazol-5-yl)acetamide

To a solution of 2-(4-chlorobenzylthio)benzo[d]oxazol-5-amine (87 mg,0.30 mmol) in dry pyridine (3 mL) at room temperature was added acetylchloride (21 μL, 0.30 mmol). The resulting solution was stirred at roomtemperature for 16 h. Water was then added, the precipitate wascollected by filtration, washed with diluted aqueous hydrochloric acidand then with water. Trituration with diethyl ether afforded 40 mg (40%)of the title compound (LCMS RT=6.40 min, MH⁺ 333.1)

¹H NMR (DMSO): 10.08 (1H, s), 8.01 (1H, d, J 1.8 Hz), 7.58-7.52 (3H, m),7.43-7.35 (3H, m), 4.60 (2H, s), 2.06 (3H, s)

The compound below was prepared following the same general method.

N-(2-(4-Chlorobenzylthio)benzo[d]oxazol-5-yl)isobutyramide

LCMS RT=7.00 min, MH⁺ 361.1; ¹H NMR (DMSO): 9.96 (1H, s), 8.04 (1H, d, J1.8 Hz), 7.58-7.52 (3H, m), 7.43-7.39 (3H, m), 4.60 (2H, s), 2.65-2.60(1H, m), 1.12 (6H, d, J 6.8 Hz)

Method 21 (Compound XX) 2-Chloro-5-nitrobenzo[d]oxazole

To a solution of 5-nitrobenzo[d]oxazole-2(3H)-thione (2.52 g, 12.86mmol) in phosphorous oxychloride (21 mL) was added phosphorouspentachloride (2.68 g, 12.86 mmol) in one portion. The mixture was thenheated to 100° C. for 2.5 h. After cooling, the excess of phosphorousoxychloride was removed in vacuo and the resulting mixture was usedcrude without characterisation.

Method 22 (Compound XXI) 5-Nitro-2-(thiophen-2-yl)benzo[d]oxazole

A mixture of 2-chloro-5-nitrobenzo[d]oxazole (404 mg, 2.04 mmol),2-(tributylstannyl)-thiophene (648 μL, 2.04 mmol) andtetrakis(triphenylphosphine)palladium (0) (40.8 mg) in dioxane (12.2 mL)was heated at 100° C. for 16 h under nitrogen. Ethyl acetate was added,the organic layer was washed with water, dried over anhydrous MgSO₄ andevaporated. The resulting solid was purified by column chromatographyeluting with ethyl acetate/hexanes 10:90 v/v, and then purified byreverse phase HPLC to afford 3 mg (2%) of the title product (LCMSRT=6.95 min)

¹H NMR (DMSO): 8.54 (1H, d, J 2.2 Hz), 8.27 (1H, dd, J 9.0 2.3 Hz), 8.04(1H, dd, J 5.4 1.2 Hz), 7.93 (1H, d, J 9.0 Hz), 7.69 (1H, dd, J 3.7 1.2Hz), 7.29 (1H, dd, J 5.4 3.7 Hz)

Method 23 (Compounds XXII)5-Amino-2-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)phenol

To polyphosphoric acid at 130° C. were added4,5-dimethylbenzene-1,2-diamine (500 mg, 3.67 mmol) and4-amino-2-hydroxybenzoic acid (562 mg, 3.67 mmol), and the resultingmixture was then heated to 130° C. for 16 h. The solution was thenpoured into water and the resulting precipitate was dissolved in ethylacetate and washed with Na₂CO₃. The aqueous layer was separated andextracted twice with ethyl acetate. The combined organic layers weredried over anhydrous MgSO₄ and evaporated. The resulting solid waspurified by column chromatography eluting with ethyl acetate/hexanes50:50 v/v to afford 260 mg (28%) of the title compound (LCMS RT=6.14min, MH⁺ 254.1)

¹H NMR (DMSO): 13.07 (1H, s), 12.40 (1H, s), 7.61 (1H, d, J 8.3 Hz),7.35 (1H, s), 7.24 (1H, s), 6.19 (1H, dd, J 8.5 2.2 Hz), 6.12 (1H, d, J2.1 Hz), 5.59 (2H, s), 2.32 (3H, s), 2.30 (3H, s)

All compounds below were prepared following the same general method.

2-(3-Methyl-4-nitrophenyl)-1H-benzo[d]imidazole

LCMS RT=5.87 min, MH⁺ 254.1; ¹H NMR (DMSO): 13.20 (1H, br), 9.31 (1H,s), 8.21-8.19 (2H, m), 7.67-7.64 (2H, m), 7.28-7.25 (2H, m), 2.65 (3H,s)

2-(6-Nitro-1H-benzo[d]imidazol-2-yl)phenol

LCMS RT=6.48 min, MH⁺ 256.0; ¹H NMR (DMSO): 13.50 (1H, br), 12.40 (1H,br), 8.56 (1H, s), 8.20-8.14 (2H, m), 7.84 (1H, d, J 8.8 Hz), 7.48-7.43(1H, m), 7.12-7.04 (2H, m)

2-(4-Chlorophenyl)-6-nitro-1H-benzo[d]imidazole

LCMS RT=6.24 min, MH⁺ 273.9; ¹H NMR (DMSO): 13.80 (1H, br), 8.54 (1H, d,J 2.1 Hz), 8.29 (2H, d, J 8.6 Hz), 8.21 (1H, dd, J 8.9 2.2 Hz), 7.84(1H, d, J 8.9 Hz), 7.75 (2H, d, J 8.5 Hz)

Method 24 (Compound XXIIb) 2-(5-Amino-1H-benzo[d]imidazol-2-yl)phenol

To 2-(5-nitro-1H-benzo[d]imidazol-2-yl)phenol (90 mg, 0.35 mmol) inethyl acetate/water/acetic acid 1:1:0.01 v/v/v (10 mL) was addedpalladium on carbon (15 mg). The reaction vessel was purged three timeswith nitrogen, followed by three times with hydrogen, and then leftstirring under hydrogen for 2 h. The reaction vessel was finally purgedthree times with nitrogen, before filtration on a pad of Celite®, whichwas washed with ethyl acetate. The organic layer was washed withsaturated aqueous NaHCO₃. The combined organic layers were dried overanhydrous MgSO₄ and evaporated. The resulting solid was purified bycolumn chromatography eluting with ethyl acetate/hexanes 2:1 v/v toafford 60 mg (76%) of the title compound (LCMS RT=5.39 min, MH⁺ 226.1)

¹H NMR (DMSO): 13.28 (1H, br), 12.63 (1H, br), 7.72 (1H, d, J 8.4 Hz),7.33-7.28 (2H, m), 6.99-6.94 (2H, m), 6.71-6.58 (2H, m), 5.12 (2H, s)

Method 25 (Compounds XXIII)N-(2-p-Tolyl-1H-benzo[d]imidazol-5-yl)butyramide

To a solution of 2-p-tolyl-1H-benzo[d]imidazol-5-amine (150 mg, 0.67mmol) in pyridine (10 mL) at room temperature was added butyryl chloride(77 μL, 0.74 mmol). The resulting mixture was stirred at roomtemperature for 16 h. Ethyl acetate was added and the organic layer waswashed twice with saturated aqueous copper sulfate, followed by sodiumbicarbonate and brine. The combined organic layers were dried overanhydrous MgSO₄ and evaporated. The resulting solid was purified bycolumn chromatography eluting with ethyl acetate/hexanes 50:50 v/v toafford 56 mg (28%) of the title compound (LCMS RT=6.96 min, MH 294.0)

¹H NMR (DMSO): 12.68 (1H, br), 9.87 (1H, s), 8.08-8.00 (3H, m),7.52-7.20 (4H, m), 2.38 (3H, s), 2.31 (2H, t, J 7.3 Hz), 1.70-1.58 (2H,m), 0.94 (3H, t, J 7.4 Hz)

All compounds below were prepared following the same general method.

N-(2-p-Tolyl-1H-benzo[d]imidazol-5-yl)isobutyramide

LCMS RT=5.43 min, MH⁺ 294.1; ¹H NMR (DMSO): 12.67 (1H, br), 9.91 (1H,s), 8.08-8.01 (3H, m), 7.50-7.28 (4H, m), 4.03 (1H, q, J 7.2 Hz), 2.38(3H, s), 1.13 (6H, d, J 6.8 Hz)

N-(2-(4-Chlorophenyl)-1H-benzo[d]imidazol-5-yl)butyramide

LCMS RT=5.54 min, MH 314.0; ¹H NMR (DMSO): 12.85 (1H, br), 9.90 (1H, s),8.14 (3H, d, J 8.6 Hz), 7.62 (2H, d, J 8.7 Hz), 7.53 (1H, br), 7.25 (1H,br), 2.32 (2H, t, J 7.1 Hz), 1.71-1.58 (2H, m), 0.94 (3H, t, J 7.5 Hz)

N-(2-Phenyl-1H-benzo[d]imidazol-5-yl)isobutyramide

LCMS RT=5.32 min, MH⁺ 280.0; ¹H NMR (DMSO): 12.80 (1H, br), 9.85 (1H,s), 8.16-8.09 (3H, m), 7.58-7.47 (4H, m), 7.28 (1H, d, J 8.1 Hz),2.68-2.60 (1H, m), 1.13 (6H, d, J 6.9 Hz)

N-(2-Phenyl-1H-benzo[d]imidazol-5-yl)butyramide

LCMS RT=5.32 min, MH 280.0; ¹H NMR (DMSO): 12.77 (1H, br), 9.90 (1H, s),8.15-8.12 (3H, m), 7.58-7.45 (4H, m), 7.26 (1H, br), 2.31 (2H, t, J 7.1Hz), 1.71-1.58 (2H, m), 0.94 (3H, t, J 7.5 Hz)

N-(2-(4-Chlorophenyl)-1H-benzo[d]imidazol-5-yl)isobutyramide

LCMS RT=5.71 min, MH⁺ 314.0; ¹H NMR (DMSO): 12.89 (1H, br), 9.86 (1H,s), 8.18-8.10 (3H, m), 7.62 (2H, d, J 8.8 Hz), 7.52 (1H, d, J 8.8 Hz),7.29 (1H, d, J 8.3 Hz), 2.66-2.60 (1H, m), 1.13 (6H, d, J 6.9 Hz)

Method 26 (Compound XXIV) 2-Amino-4-nitrobenzenethiol

2-Fluoro-5-nitroaniline (1 g, 6.41 mmol), sodium sulfide nonahydrate(1.7 g, 7.05 mmol), sodium bicarbonate (600 mg, 7.05 mmol) and water (15mL) were combined and heated in the microwave at 125° C. for 5 min.After cooling, dichloromethane was added, and the organic layer waswashed with 2M aqueous hydrochloric acid and then brine. The combinedorganic layers were dried over anhydrous MgSO₄ and evaporated to afford1.1 g (33%) of the title compound.

¹H NMR (DMSO): 7.61-7.55 (2H, m), 7.47 (1H, d, J 8.2 Hz), 7.31 (3H, s)

Method 27 (Compound XXV) 2-(2-Chlorophenyl)-5-nitrobenzo[d]thiazole

2-Amino-4-nitrobenzenethiol (315 mg, 1.85 mmol), 2-chlorobenzoic acid(290 mg, 1.85 mmol) and Eaton's reagent (5 mL) were combined and heatedin the microwave at 130° C. for 10 min. After cooling, the mixture waspoured into water and basified with 5M aqueous sodium hydroxide to givea precipitate, which was filtered off and dried to afford 530 mg (98%)of the title compound.

¹H NMR (DMSO): 8.93 (1H, d, J 2.2 Hz), 8.53 (1H, d, J 8.9 Hz), 8.37 (1H,dd, J 8.9 2.2 Hz), 8.29 (1H, dd, J 7.4 1.9 Hz), 7.78-7.75 (1H, m),7.70-7.60 (2H, m)

Method 28 (Compound XXVI) N-(2-Chloro-5-nitrophenyl)-4-methylbenzamide

To 2-chloro-5-nitroaniline (2 g, 11.59 mmol) in pyridine (5 mL) at roomtemperature was added 4-methylbenzoyl chloride (1.6 mL, 12.17 mmol),followed by pyridine (5 mL). The mixture was then stirred at roomtemperature for 16 h. Ethyl acetate was then added to the solution togive a precipitate, which was filtered off and washed twice with ethylacetate, and then hexanes. The resulting solid was then washed withaqueous sodium bicarbonate, 1M aqueous sodium hydroxide, water andhexanes to afford (1.4 g, 42%) of the title compound.

¹H NMR (DMSO): 10.26 (1H, s), 8.58 (1H, d, J 2.8 Hz), 8.11 (1H, dd, J8.9 2.8 Hz), 7.93 (2H, d, J 8.2 Hz), 7.87 (1H, d, J 8.9 Hz), 7.38 (2H,d, J 8.0 Hz), 2.41 (3H, s)

Method 29 (Compound XXV) 5-Nitro-2-p-tolylbenzo[d]thiazole

Sodium sulfide nonahydrate (875 mg, 3.78 mmol) and sulfur (120 mg, 3.78mmol) were heated until molten. The water was driven off with nitrogento give a solid. The obtained solid was added in portions toN-(2-chloro-5-nitrophenyl)-4-methylbenzamide (1 g, 3.44 mmol) in ethanol(20 mL) at 85° C. The solution was stirred at 85° C. for 3 h. Aftercooling, 2M aqueous HCl was added, and the solution was extracted threetimes with ethyl acetate. The combined organic layers were dried overanhydrous MgSO₄ and evaporated. The resulting solid was purified bycolumn chromatography eluting with ethyl acetate/hexanes 10:90 v/v toafford 400 mg (43%) of the title compound.

¹H NMR (DMSO): 8.81 (1H, d, J 2.2 Hz), 8.45 (1H, d, J 8.8 Hz), 8.29 (1H,dd, J 8.8 2.3 Hz), 8.06 (2H, d, J 8.2 Hz), 7.44 (2H, d, J 8.0 Hz), 2.42(3H, s)

Method 30 (Compounds XXVII) 2-p-Tolylbenzo[d]thiazol-5-amine

5-Nitro-2-p-tolylbenzo[d]thiazole (400 mg, 1.48 mmol) was suspended inethanol/water (8 mL/4 mL) and heated at 80° C. Ammonium chloride (160mg, 2.96 mmol) and iron powder (414 mg, 7.40 mmol) were added to thesuspension, and the mixture was left stirring at 80° C. for 75 min.After cooling, the solution was filtrated through a pad of Celite® andthe pad washed with ethanol. Water was added to the filtrate, ethanolwas evaporated and the remaining aqueous layer was extracted with ethylacetate. The combined organic layers were dried over anhydrous MgSO₄ andevaporated to afford 220 mg (62%) of the title compound (LCMS RT=6.51min, MH⁺ 241.0)

¹H NMR (DMSO): 7.91 (2H, d, J 8.1 Hz), 7.68 (1H, d, J 8.6 Hz), 7.35 (2H,d, J 8.0 Hz), 7.15 (1H, d, J 2.0 Hz), 6.77 (1H, dd, J 8.6 2.0 Hz), 5.32(2H, s), 2.39 (3H, s)

All compounds below were prepared following the same general method.

2-Phenylbenzo[d]thiazol-5-amine

LCMS RT=6.1 min, MH⁺ 227.1; ¹H NMR (DMSO): 8.04-8.01 (2H, m), 7.71 (1H,d, J 8.5 Hz), 7.56-7.53 (3H, m), 7.18 (1H, d, J 2.1 Hz), 6.79 (1H, dd, J8.6 2.3 Hz), 5.33 (2H, s)

2-(4-Chlorophenyl)benzo[d]thiazol-5-amine

LCMS RT=6.72 min, MH⁺ 260.7; ¹H NMR (DMSO): 8.04 (2H, d, J 8.7 Hz), 7.72(1H, d, J 8.6 Hz), 7.61 (2H, d, J 8.7 Hz), 7.17 (1H, d, J 2.0 Hz), 6.80(1H, dd, J 8.6 2.2 Hz), 5.35 (2H, s)

2-(2-Chlorophenyl)benzo[d]thiazol-5-amine

LCMS RT=6.49 min, MH⁺ 260.8; ¹H NMR (DMSO): 8.19-8.16 (1H, m), 7.76 (1H,d, J 8.6 Hz), 7.69-7.66 (1H, m), 7.56-7.52 (2H, m), 7.22 (1H, d, J 2.0Hz), 6.85 (1H, dd, J 8.6 2.1 Hz), 5.37 (2H, s)

2-(3-Chlorophenyl)benzo[d]thiazol-5-amine

LCMS RT=6.79 min, MH⁺ 260.8; ¹H NMR (DMSO): 8.05-8.04 (1H, m), 7.96 (1H,dt, J 7.0 1.7 Hz), 7.74 (1H, d, J 8.6 Hz), 7.64-7.55 (2H, m), 7.19 (1H,d, J 1.7 Hz), 6.82 (1H, dd, J 8.6 2.2 Hz), 5.37 (2H, s)

2-(3,4-Dichlorophenyl)benzo[d]thiazol-5-amine

LCMS RT=7.49 min, MH⁺ 294.9; ¹H NMR (DMSO): 8.24 (1H, d, J 2.1 Hz), 8.00(1H, dd, J 8.4 2.1 Hz), 7.82 (1H, d, J 8.4 Hz), 7.76 (1H, d, J 8.6 Hz),7.20 (1H, d, J 1.9 Hz), 6.84 (1H, dd, J 8.6 2.2 Hz), 5.41 (2H, s)

2-(2,3-Dichlorophenyl)benzo[d]thiazol-5-amine

LCMS RT=7.00 min, MH⁺ 294.9; ¹H NMR (DMSO): 8.08 (1H, dd, J 7.9 1.6 Hz),7.84 (1H, dd, J 8.0 1.6 Hz), 7.78 (1H, d, J 8.6 Hz), 7.55 (1H, t, J 8.0Hz), 7.22 (1H, d, J 2.0 Hz), 6.87 (1H, dd, J 8.6 2.2 Hz), 5.38 (2H, s)

Method 31 (Compounds XXVIII) N-(2-p-Tolylbenzo[d]thiazol-5-yl)butyramide

To a solution of 2-p-tolylbenzo[d]thiazol-5-amine (110 mg, 0.46 mmol) inpyridine (3 mL) at room temperature was added butyryl chloride (53 μL,0.50 mmol). The resulting mixture was stirred at room temperature for 2days. Ethyl acetate was added and the organic layer was washed withsaturated aqueous copper sulfate, followed by aqueous sodium bicarbonateand finally with brine. The combined organic layers were dried overanhydrous MgSO₄ and evaporated. The resulting solid was purified bycolumn chromatography eluting with ethyl acetate/hexanes 50:50 v/v toafford 25 mg (18%) of the title compound (LCMS RT=7.10 min, MH⁺ 311.0)

¹H NMR (DMSO): 10.12 (1H, s), 8.43 (1H, d, J 1.8 Hz), 8.02-7.96 (3H, m),7.58 (1H, dd, J 8.6 2.0 Hz), 7.38 (2H, d, J 8.0 Hz), 2.40 (3H, s), 2.35(2H, t, J 7.5 Hz), 1.72-1.60 (2H, m), 0.95 (3H, t, J 7.4 Hz)

All compounds below were prepared following the same general method.

N-(2-p-Tolylbenzo[d]thiazol-5-yl)isobutyramide

LCMS RT=7.06 min, MH⁺ 311.0; ¹H NMR (DMSO): 10.08 (1H, s), 8.44 (1H, d,J 1.3 Hz), 8.03-7.96 (3H, m), 7.60 (1H, dd, J 8.7 1.6 Hz), 7.38 (2H, d,J 8.0 Hz), 2.69-2.60 (1H, m), 2.40 (3H, s), 1.15 (6H, d, J 6.8 Hz)

N-(2-Phenylbenzo[d]thiazol-5-yl)isobutyramide

LCMS RT=6.56 min, MH⁺ 297.0; ¹H NMR (DMSO): 10.07 (1H, s), 8.47 (1H, d,J 1.8 Hz), 8.11-8.07 (2H, m), 8.04 (1H, d, J 8.6 Hz), 7.64-7.56 (4H, m),2.70-2.61 (1H, m), 1.15 (6H, d, J 6.8 Hz)

N-(2-(4-Chlorophenyl)benzo[d]thiazol-5-yl)isobutyramide

LCMS RT=7.42 min, MH⁺ 331.0; ¹H NMR (DMSO): 10.08 (1H, s), 8.47 (1H, d,J 1.9 Hz), 8.10 (2H, d, J 8.6 Hz), 8.05 (1H, d, J 8.7 Hz), 7.67-7.61(3H, m), 2.70-2.60 (1H, m), 1.15 (6H, d, J 6.8 Hz)

N-(2-(2-Chlorophenyl)benzo[d]thiazol-5-yl)isobutyramide

LCMS RT=6.99 min, MH⁺ 330.9; ¹H NMR (DMSO): 10.12 (1H, s), 8.55 (1H, d,J 1.9 Hz), 8.25-8.22 (1H, m), 8.10 (1H, d, J 8.8 Hz), 7.74-7.55 (4H, m),2.72-2.63 (1H, m), 1.17 (6H, d, J 6.8 Hz)

N-(2-(3-Chlorophenyl)benzo[d]thiazol-5-yl)isobutyramide

LCMS RT=7.34 min, MH⁺ 330.9; ¹H NMR (DMSO): 10.11 (1H, s), 8.50 (1H, d,J 1.7 Hz), 8.13-8.03 (3H, m), 7.69-7.60 (3H, m), 2.71-2.62 (1H, m), 1.17(6H, d, J 6.8 Hz)

N-(2-(3,4-Dichlorophenyl)benzo[d]thiazol-5-yl)isobutyramide

LCMS RT=8.21 min, MH⁺ 364.7; ¹H NMR (DMSO): 10.11 (1H, s), 8.52-8.50(1H, m), 8.30 (1H, d, J 2.1 Hz), 8.10-8.04 (2H, m), 7.85 (1H, d, J 8.4Hz), 7.69-7.64 (1H, m), 2.71-2.64 (1H, m), 1.17 (6H, d, J 6.8 Hz)

N-(2-(2,3-Dichlorophenyl)benzo[d]thiazol-5-yl)isobutyramide

LCMS RT=7.62 min, MH⁺ 364.9; ¹H NMR (DMSO): 10.12 (1H, s), 8.55 (1H, d,J 1.7 Hz), 8.14-8.10 (2H, m), 7.88 (1H, dd, J 8.0 1.4 Hz), 7.67 (1H, dd,J 8.8 2.0 Hz), 7.58 (1H, t, J 8.0 Hz), 2.70-2.61 (1H, m), 1.15 (6H, d, J6.8 Hz)

Method 32 (Compound XXIX) 4-Chloro-N-(4-(methylthio)phenyl)benzamide

To 4-(methylthio)aniline (1 mL, 8.19 mmol) in dichloromethane (20 mL)was added pyridine (2 mL, 24.6 mmol). The resulting solution was cooledto 10-15° C. and 4-chlorobenzoyl chloride (1.14 mL, 9.00 mmol) was addedover 5 min. The mixture was stirred at room temperature for 90 min. Theprecipitate was filtered off, washed with dichloromethane, 1M aqueoussodium hydroxide solution and 1M aqueous hydrochloric acid solution toafford 2.12 g (93%) of the title compound.

¹H NMR (DMSO): 10.31 (1H, s), 7.98 (2H, d, J 8.7 Hz), 7.73 (2H, d, J 8.8Hz), 7.61 (2H, d, J 8.8 Hz), 7.28 (2H, d, J 8.8 Hz), 2.47 (3H, s)

Method 33 (Compound XXX) 4-Chloro-N-(4-(methylthio)phenyl)benzothioamide

A suspension of 4-chloro-N-(4-(methylthio)phenyl)benzamide (1 g, 3.60mmol) and Lawesson's reagent (875 mg, 2.16 mmol) in toluene (25 mL) washeated to 11 0° C. for 16 h. After cooling, toluene was removed in vacuoand the resulting solid was purified by column chromatography elutingusing a gradient (hexanes to ethyl acetate/hexanes 30:70 v/v) to afford503 mg (48%) of the title compound.

LCMS RT=6.98 min, MH⁺ 294.1; ¹H NMR (DMSO): 11.80 (1H, s), 7.85 (2H, d,J 8.6 Hz), 7.78 (2H, d, J 8.7 Hz), 7.54 (2H, d, J 8.6 Hz), 7.33 (2H, d,J 8.7 Hz)

Method 34 (Compound XXXI)2-(4-Chlorophenyl)-6-(methylthio)benzo[d]thiazole

To a solution of potassium hexacyanoferrate(III) (670 mg, 2.04 mmol) inwater (5 mL) at 90° C. was added dropwise over 5 minutes a solution of4-chloro-N-(4-(methylthio)phenyl)benzothioamide (150 mg, 0.51 mmol) inethanol (2 mL) and 3M aqueous sodium hydroxide solution (1.4 mL, 4.08mmol). The resulting mixture was heated at 90° C. for 30 minutes. Aftercooling, the precipitate formed was filtered off and washed with waterto give a yellow solid. The yellow solid was purified by columnchromatography eluting using a gradient (hexanes to ethylacetate/hexanes 5:95 v/v) to afford 100 mg (67%) of the title compound(LCMS RT=9.37 min, MH⁺ 292.2)

¹H NMR (DMSO): 8.11-8.06 (3H, m), 7.98 (1H, d, J 8.6 Hz), 7.65 (2H, d, J8.7 Hz), 7.45 (1H, dd, J 8.6 1.9 Hz), 2.58 (3H, s)

Method 35 (Compound XXXII)2-(4-Chlorophenyl)-6-(methylsulfonyl)benzo[d]thiazole

To a solution of 2-(4-chlorophenyl)-6-(methylthio)benzo[d]thiazole (240mg, 0.82 mmol) in dichloromethane (20 mL) was added3-chloroperoxybenzoic acid (77% in water, 710 mg, 4.11 mmol) over 5 min.The resulting mixture was stirred at room temperature for 3 h. 1Maqueous sodium hydroxide solution was added carefully, and the mixturewas then stirred for 5 min. The organic layer was then washed with 1Maqueous sodium hydroxide solution, dried over anhydrous MgSO₄ andevaporated. The resulting solid was recrystallised from hot ethylacetate to afford 125 mg (47%) of the title compound (LCMS RT=6.81 min,MH⁺ 324.0)

¹H NMR (CDCl₃): 8.61 (1H, dd, J 1.8 0.4 Hz), 8.26 (1H, dd, J 8.6 0.5Hz), 8.14-8.09 (3H, m), 7.57 (2H, d, J 8.6 Hz), 3.19 (3H, s)

Method 36 (Compounds XXXIII) 2-(4-Chlorophenyl)-5-phenyl-1H-indole

To a suspension of 5-bromo-2-(4-chlorophenyl)-1H-indole (200 mg, 0.65mmol) in dioxane/water 4:1 v/v (5 mL) was added phenylboronic acid (87mg, 0.72 mmol) and a few milligrams oftetrakis(triphenylphosphine)palladium(0). The resulting suspension washeated in the microwave at 160° C. for 15 min. After cooling, thereaction was poured into water to give a precipitate, which was filteredoff and washed with water. The resulting solid was purified by columnchromatography eluting using a gradient (hexanes to ethylacetate/hexanes 30:70 v/v), followed by a recrystallisation from hotethyl acetate to afford 21 mg (11%) of the title compound (LCMS RT=8.54min, MH⁺ 304.1)

¹H NMR (DMSO): 11.68 (1H, s), 7.91 (2H, d, J 8.6 Hz), 7.81 (1H, d, J 1.1Hz), 7.70-7.66 (2H, m), 7.55 (2H, d, J 8.6 Hz), 7.50-7.41 (4H, m),7.33-7.28 (1H, m), 7.01 (1H, d, J 1.2 Hz)

The compound below was prepared following the same general method.

N-(4-(2-(4-Chlorophenyl)-1H-indol-5-yl)phenyl)acetamide

LCMS RT=6.69 min, MH⁺ 361.0; ¹H NMR (DMSO): 11.64 (1H, s), 9.98 (1H, s),7.91 (2H, d, J 8.6 Hz), 7.77 (1H, d, J 1.0 Hz), 7.68-7.60 (4H, m), 7.54(2H, d, J 8.6 Hz), 7.46 (1H, d, J 8.3 Hz), 7.41 (1H, dd, J 8.5 1.6 Hz),6.99 (1H, d, J 1.5 Hz), 2.07 (3H, s)

Method 37 (Compound XXXIV) 1-Methyl-6-nitro-1H-indole

To a solution of 6-nitro-1H-indole (100 mg, 0.62 mmol) and 18-Crown-6(180 mg, 0.68 mmol) in anhydrous tetrahydrofuran (2 mL) at roomtemperature was slowly added potassium tert-butoxide (76 mg, 0.68 mmol)followed by methyl iodide (42 μL, 0.68 mmol). The solution was stirredat room temperature for 30 min. Tetrahydrofuran was removed in vacuo.Ethyl acetate was added, and the organic layer was washed with water andthen brine. The combined organic layers were dried over anhydrous MgSO₄and evaporated to afford 91 mg (84%) of the title compound.

¹H NMR (CDCl₃): 8.16 (1H, d, J 1.8 Hz), 7.85 (1H, dd, J 8.7 1.9 Hz),7.49 (1H, d, J 8.7 Hz), 7.19 (1H, d, J 3.1 Hz), 6.43 (1H, dd, J 3.1 0.9Hz), 3.74 (3H, s)

Method 38 (Compound XXXV) 1-Methyl-1H-indol-6-amine

1-methyl-6-nitro-1H-indole (90 mg, 0.51 mmol), ammonium chloride (55 mg,1.02 mmol) and iron powder (143 mg, 2.55 mmol) were suspended inethanol/water (2 mL/1 mL) and heated at 70° C. for 2 h. After cooling,the solution was filtrated through a pad of Celite®, which was washedwith ethanol. Ethyl acetate was added to the filtrate and the organiclayer was washed with water twice. The combined organic layers weredried over anhydrous MgSO₄ and evaporated to afford 30 mg (37%) of thetitle compound

¹H NMR (DMSO): 7.17 (1H, d, J 8.4 Hz), 6.93 (1H, d, J 3.1 Hz), 6.51-6.49(1H, m), 6.41 (1H, dd, J 8.3 1.9 Hz), 6.16 (1H, d, J 3.1 Hz), 4.76 (2H,s), 3.60 (3H, s)

Method 39 (Compounds XXXVI) N-(1-Methyl-1H-indol-6-yl)isobutyramide

To a solution of 1-methyl-1H-indol-6-amine (45 mg, 0.31 mmol) inpyridine (2 mL) at room temperature was added isobutyryl chloride (35μL, 0.34 mmol). The resulting mixture was stirred at room temperaturefor 16 h. Ethyl acetate was added and the organic layer was washed threetimes with brine. The combined organic layers were dried over anhydrousMgSO₄ and evaporated to afford 24.3 mg (36%) of the title compound (LCMSRT=5.73 min, MH⁺ 217.2)

¹H NMR (DMSO): 9.78 (1H, s), 7.96 (1H, m), 7.44 (1H, d, J 8.4 Hz), 7.24(1H, d, J 3.1 Hz), 7.08 (1H, dd, J 8.4 1.7 Hz), 6.35 (1H, dd, J 3.0 0.7Hz), 3.73 (3H, s), 2.68-2.61 (1H, m), 1.13 (6H, d, J 6.9 Hz)

The compound below was prepared following the same general method.

N-(1-Benzyl-1H-indol-6-yl)isobutyramide

LCMS RT=6.36 min, MH⁺ 293.2; ¹H NMR (DMSO): 9.73 (1H, s), 7.90 (1H, m),7.45 (1H, d, J 8.5 Hz), 7.41 (1H, d, J 3.1 Hz), 7.34-7.24 (3H, m),7.14-7.10 (3H, m), 6.42 (1H, d, J 3.2 Hz), 5.35 (2H, s), 1.08 (6H, d, J6.8 Hz)

Method 40 (Compound XXXVII) N-(2-Hydroxy-5-nitrophenyl)butyramide

To a solution of 2-amino-4-nitrophenol (log, 64.9 mmol) indichloromethane (250 mL) under nitrogen at 0° C. was added pyridine(10.5 mL, 129.9 mmol) followed by butyryl chloride (7.05 mL, 68.2 mmol)over a period of 5 min. After 30 min at 0° C., the solution was leftwarming up to room temperature for 2 days. The organic layer was washedwith aqueous copper sulfate solution and brine. Insoluble material fromthe aqueous layer was filtered off and washed with water to afford 4.95g (34%) of the title compound.

¹H NMR (DMSO): 11.64 (1H, br), 9.37 (1H, s), 8.95 (1H, d, J 2.8 Hz),7.89 (1H, dd, J 8.9 2.8 Hz), 7.02 (1H, d, J 8.9 Hz), 2.43 (2H, t, J 7.4Hz), 1.67-1.55 (2H, m), 0.92 (3H, t, J 7.5 Hz)

Method 41 (Compound XXXVIII) 2-Butyramido-4-nitrophenyltrifluoromethanesulfonate

To a solution of sodium hydride (220 mg, 5.58 mmol) in dry acetonitrile(40 mL) at 0° C. under nitrogen was added a solution ofN-(2-hydroxy-5-nitrophenyl)butyramide (1 g, 4.46 mmol) in dryacetonitrile (90 mL). The solution was then stirred at 0° C. for 30 min.Trifluoromethanesulfonic anhydride (825 μL, 4.90 mmol) was addeddropwise at 0° C. over a period of 10 min. After 3 h at 0° C., thesolution was stirred at room temperature for 3 h. Water was added, andthe aqueous layer was extracted with ethyl acetate. The organic layerwas then washed with dilute aqueous hydrochloric acid, aqueous sodiumbicarbonate and brine. The combined organic layers were dried overanhydrous MgSO₄ and evaporated. The resulting oil was purified by columnchromatography eluting using a gradient (hexanes to ethylacetate/hexanes 25:75 v/v) to afford 860 mg (54%) of the title compound.

¹H NMR (CDCl₃): 9.37 (1H, d, J 2.8 Hz), 8.09 (1H, dd, J 9.1 2.8 Hz),7.53 (2H, d, J 9.1 Hz), 2.50 (2H, t, J 7.6 Hz), 1.91-1.78 (2H, m), 1.09(3H, t, J 7.5 Hz)

Method 42 (Compound XXXIX) N-(5-Nitro-2-(phenylethynyl)phenyl)butyramide

To a solution of 2-butyramido-4-nitrophenyl trifluoromethanesulfonate(860 mg, 2.42 mmol) in dry acetonitrile (30 mL) under nitrogen was addedtetrabutylammonium iodide (1.34 g, 3.62 mmol),tetrakis(triphenylphosphine)palladium(0) (280 mg, 0.24 mmol) and copperiodide (140 mg, 0.72 mmol). Triethylamine (6 mL) was then added,followed by phenyl acetylene (530 μL, 4.83 mmol). The resulting solutionwas stirred at room temperature for 2 h. Ammonium chloride was thenadded to quench the reaction, and the aqueous layer was extracted withethyl acetate. The organic layer was washed with brine. The combinedorganic layers were dried over anhydrous MgSO₄ and evaporated. Theresulting solid was purified by column chromatography eluting using agradient (hexanes to ethyl acetate) to afford 580 mg (78%) of the titlecompound.

¹H NMR (DMSO): 9.81 (1H, s), 8.74 (1H, d, J 2.3 Hz), 8.01 (1H, dd, J 8.62.4 Hz), 7.83 (1H, d, J 8.6 Hz), 7.70-7.67 (2H, m), 7.52-7.49 (3H, m),1.73-1.61 (2H, m), 0.96 (3H, t, J 7.5 Hz)

Method 43 (Compound XLa) 6-Nitro-2-phenyl-1H-indole

To a solution of N-(5-nitro-2-(phenylethynyl)phenyl)butyramide (580 mg,1.88 mmol) in 1-Methyl-2-pyrrolidinone (20 mL) under nitrogen was addedpotassium tert-butoxide (243 mg, 2.16 mmol). The resulting solution washeated at 70° C. for 6 h, and then left at room temperature for 16 h.Water was added and the aqueous layer was extracted several times withethyl acetate. The combined organic layers were washed 10 times withwater, 3 times with brine, dried over anhydrous MgSO₄ and evaporated.The resulting material was purified by column chromatography elutingwith ethyl acetate/hexanes 15:85 v/v to afford 175 mg (39%) of the titlecompound.

¹H NMR (DMSO): 12.35 (1H, s), 8.30 (1H, d, J 2.1 Hz), 7.97-7.90 (3H, m),7.73 (1H, d, J 8.9 Hz), 7.57-7.52 (2H, m), 7.47-7.42 (1H, m), 7.17 (1H,dd, J 2.0 0.8 Hz)

Method 44 (Compound XLb) 1-Methyl-6-nitro-2-phenyl-1H-indole

To a solution of 6-nitro-2-phenyl-1H-indole (106 mg, 0.44 mmol) and18-Crown-6 (130 mg, 0.49 mmol) in anhydrous tetrahydrofuran (2 mL) atroom temperature was added potassium tert-butoxide (55 mg, 0.49 mmol)followed by methyl iodide (31 μL, 0.49 mmol). The solution was stirredat room temperature for 30 min. Tetrahydrofuran was removed in vacuo.Ethyl acetate was added, and the organic layer was washed with water andthen brine. The combined organic layers were dried over anhydrous MgSO₄and evaporated to afford 110 mg (98%) of the title compound.

¹H NMR (DMSO): 8.60 (1H, d, J 2.1 Hz), 8.03 (1H, dd, J 8.8 2.1 Hz), 7.82(1H, d, J 8.7 Hz), 7.74-7.71 (2H, m), 7.67-7.57 (3H, m), 6.87 (1H, d, J0.8 Hz), 3.95 (3H, s)

Method 45 (Compound XLI) 2-Phenyl-1H-indol-6-amine

6-Nitro-2-phenyl-1H-indole (175 mg, 0.73 mmol), ammonium chloride (80mg, 1.47 mmol) and iron powder (205 mg, 3.68 mmol) were suspended inethanol/water (4 mL/2 mL) and heated at 70° C. for 2 h. After cooling,the solution was filtrated through a pad of Celite®, which was washedwith ethanol. The organic layer was evaporated into vacuo to obtain asolid, which was purified by column chromatography eluting using agradient (ethyl acetate/hexanes 10:90 v/v to ethyl acetate/hexanes 50:50v/v) to afford 54 mg (35%) of the title compound.

¹H NMR (DMSO): 10.88 (1H, s), 7.76-7.72 (2H, m), 7.39 (2H, t, J 7.9 Hz),7.23-7.16 (2H, m), 6.67 (1H, dd, J 2.0 0.7 Hz), 6.59-6.57 (1H, m), 6.39(1H, dd, J 8.4 2.0 Hz), 4.82 (2H, s)

Method 46 (Compounds XLII) N-(2-Phenyl-1H-indol-6-yl)isobutyramide

To a solution of 2-phenyl-1H-indol-6-amine (54 mg, 0.26 mmol) inpyridine (2 mL) at room temperature was added isobutyryl chloride (30μL, 0.29 mmol). The resulting mixture was stirred at room temperaturefor 2 days. When water was added, a precipitate was formed. This solidwas recrystallised from hot ethyl acetate to afford 15 mg (21%) of thetitle compound (LCMS RT=6.27 min, MH⁺ 279.0)

¹H NMR (DMSO): 11.40 (1H, s), 9.74 (1H, s), 8.02 (1H, s), 7.82 (2H, d, J7.5 Hz), 7.47-7.40 (3H, m), 7.28 (1H, t, J 7.3 Hz), 7.07 (1H, dd, J 8.51.6 Hz), 6.83 (1H, d, J 1.1 Hz), 2.67-2.60 (1H, m), 1.13 (6H, d, J 6.7Hz)

The compound below was prepared following the same general method.

N-(1-Methyl-2-phenyl-1H-indol-6-yl)isobutyramide

LCMS RT=6.66 min, MH⁺ 293.2; ¹H NMR (DMSO): 9.83 (1H, s), 8.02 (1H, s),7.61-7.39 (6H, m), 7.13 (1H, dd, J 8.5 1.7 Hz), 6.50 (1H, d, J 0.5 Hz),3.69 (3H, s), 2.69-2.60 (1H, m), 1.13 (6H, d, J 6.8 Hz)

Method 47 (Compound XLIIIa) 5-Nitro-2-phenylbenzofuran

A solution of 2-iodo-4-nitrophenol (500 mg, 1.89 mmol), prolinol (573mg, 5.66 mmol), palladium on carbon (60 mg, 0.06 mmol),triphenylphosphine (59.4 mg, 0.226 mmol) and copper iodide (22 mg, 0.113mmol) in water (6 mL) was stirred for 1 h at room temperature.Ethynylbenzene (482 mg, 4.72 mmol) was slowly added, and the resultingmixture was heated at 80° C. for 3 h. After cooling, ethyl acetate wasadded, and the mixture was passed through a pad of Celite®. The filtratewas washed with water; the combined organic layers were dried overanhydrous MgSO₄ and evaporated. The resulting material was purified bycolumn chromatography eluting with ethyl acetate/hexanes 1:40 v/v toafford 134 mg (30%) of the title compound.

¹H NMR (DMSO): 8.62 (1H, d, J 2.4 Hz), 8.23 (1H, dd, J 9.1 2.5 Hz),8.00-7.96 (2H, m), 7.89 (1H, d, J 9.0 Hz), 7.66 (1H, d, J 0.4 Hz),7.60-7.46 (3H, m)

Method 48 (Compound XLIIIb) 2-Phenylbenzofuran-5-amine

To 5-Nitro-2-phenylbenzofuran (250 mg, 1.04 mmol) in ethanol/water 2:1v/v (12 mL) at 80° C. was added ammonium chloride (112 mg, 2.09 mmol)and iron powder (292 mg, 5.23 mmol). The resulting mixture was heated at80° C. for 4 h. After cooling, the solution was filtrated through a padof Celite®, which was washed with ethanol. The organic layer wasevaporated into vacuo to obtain a solid, which was then taken up inethyl acetate and washed with water. The combined organic layers weredried over anhydrous MgSO₄ and evaporated to afford 211 mg (96%) of thetitle compound.

¹H NMR (DMSO): 7.87-7.83 (2H, m), 7.50-7.44 (2H, m), 7.40-7.34 (1H, m),7.28 (1H, d, J 8.7 Hz), 7.20 (1H, d, J 0.7 Hz), 6.74 (1H, d, J 2.2 Hz),6.60 (1H, dd, J 8.7 2.3 Hz), 4.88 (2H, s)

Method 49 (Compounds XLIV) N-(2-Phenylbenzofuran-5-yl)isobutyramide

To a solution of 2-phenylbenzofuran-5-amine (210 mg, 1.00 mmol) inpyridine (5 mL) at room temperature was added isobutyryl chloride (120μL, 1.10 mmol). The resulting mixture was stirred at room temperaturefor 16 h. Ethyl acetate was added and the organic layer was washed withsaturated aqueous copper sulfate solution followed by saturated aqueouspotassium carbonate solution. The combined organic layers were driedover anhydrous MgSO₄ and evaporated. The resulting material was purifiedby column chromatography eluting using a gradient (ethyl acetate/hexanes1:3 v/v to ethyl acetate/hexanes 1:2 v/v) to afford 134 mg (48%) of thetitle compound (LCMS RT=6.81 min, MH⁺ 280.1)

¹H NMR (DMSO): 9.87 (1H, s), 8.05 (1H, s), 7.91 (2H, d, J 7.4 Hz),7.58-7.48 (3H, m), 7.45-7.38 (3H, m), 2.66-2.54 (1H, m), 1.13 (6H, d, J6.8 Hz)

The compound below was prepared following the same general method.

2-(4′-Chlorophenyl)-5-isobutyramido-benzofuran

LCMS RT=7.41 min, MH⁺ 314.2; ¹H NMR (DMSO): 9.88 (1H, s), 8.06 (1H, d, J1.9 Hz), 7.92 (2H, d, J 8.7 Hz), 7.59-7.53 (3H, m), 7.49 (1H, d, J 0.8Hz), 7.43 (1H, dd, J 9.0 2.2 Hz), 2.66-2.56 (1H, m), 1.13 (6H, d, J 6.8Hz)

Method 50 (Compound XLIV)2-Phenyl-5-(3′,3′,3′-trifluoropropanamido)benzofuran

To 3,3,3-trifluoropropanoic acid (136 mg, 1.06 mmol) in drydichloromethane (10 mL) was added HATU (468 mg, 1.23 mmol) anddiisopropylethylamine (580 μL, 3.35 mmol). The mixture was then stirredat room temperature for 10 min. 2-phenylbenzofuran-5-amine (234 mg, 1.12mmol) was then added and the resulting mixture was stirred at roomtemperature for 48 h. Ethyl acetate was added and the organic layer waswashed once with saturated aqueous water. The combined organic layerswere dried over anhydrous MgSO₄ and evaporated. The resulting solid waspurified by column chromatography eluting using a gradient (ethylacetate/hexanes 1:3 v/v to ethyl acetate/hexanes 1:1 v/v) followed bytrituration in ethyl acetate to afford 99.3 mg (28%) of the titlecompound (LCMS RT=6.62 min)

¹H NMR (DMSO): 10.37 (1H, s), 8.01 (1H, d, J 2.0 Hz), 7.92 (2H, dd, J7.5 1.5 Hz), 7.61 (1H, d, J 8.8 Hz), 7.55-7.41 (4H, m), 7.38 (1H, dd, J8.9 2.2 Hz), 3.53 (2H, q, J 11.2 Hz)

The compounds listed in Table 2, can be prepared by analogues methods tothose described above, or by literature methods known or adapted by thepersons skilled in the art.

1. Use of a compound of Formula (I)

in which A₁, A₂, A₃ and A₄, which may be the same or different,represent N or CR₁, X is a divalent group selected from O, S(O)_(n),C═W, NR₄, NC(═O)R₅ and CR₆R₇, W is O, S, NR₂₀, Y is N or CR₈, one of R₄,R₅, R₆, R₈, R₉ and NR₂₀ represents -L-R₃, in which L is a single bond ora linker group, additionally, R₁, R₃-R₉, which may be the same ordifferent, independently represent hydrogen or a substituent and R₂₀represents hydrogen, hydroxyl, alkyl optionally substituted by aryl,alkoxy optionally substituted by aryl, aryl, CN, optionally substitutedalkoxy, optionally substituted aryloxy, optionally substitute alkanoyl,optionally substituted aroyl, NO₂, NR₃₀R₃₁, in which R₃₀ and R₃₁, whichmay be the same or different, represent hydrogen, optionally substitutedalkyl or optionally substituted aryl; additionally, one of R₃₀ and R₃₁may represent optionally substituted alkanoyl or optionally substitutedaroyl, n represents an integer from 0 to 2, in addition, when anadjacent pair of A₁-A₄ each represent CR₁, then the adjacent carbonatoms, together with their substituents may form a ring B, when X isCR₆R₇, R₆ and R₇, together with the carbon atom to which they areattached may form a ring C, or a pharmaceutically acceptable saltthereof, in the manufacture of a medicament for the therapeutic and/orprophylactic treatment of Duchenne muscular dystrophy, Becker musculardystrophy or cachexia.
 2. Use according to claim 1, wherein R₃ in thecompound of formula I represents alkyl, alkoxy or aryl, each optionallysubstituted by one to three substitutents, R₂, which may be the same ordifferent.
 3. Use according to claim 1, wherein L is single bond and R₃represents: thioalkyl optionally substituted by alkyl or optionallysubstituted aryl, thioaryl, in which the aryl is optionally substituted,optionally substituted aryl, hydroxyl, NO₂, CN, NR₁₀R₁₁, halogen,SO₂R₁₂, NR₁₃SO₂R₁₄, C(═W)R₁₆, OC(═W)NR₁₀R₁₁ NR₁₅C(═W)R₁₇, R₁₀, R₁₁, R₁₂,R₁₃, R₁₄, R₁₅, R₁₆ and R₁₇, which may be the same or different,represent hydrogen, alkyl optionally substituted by optionallysubstituted aryl, optionally substituted aryl, in addition, NR₁₀R₁₁together with the nitrogen to which they are attached may form a ring,R₁₂ may have the same meaning as NR₁₀R₁₁, when R₁₇ represents NR₁₀R₁₁,that NR₁₀R₁₁ may represent hydrogen, COalkyl and CO optionallysubstituted aryl, R₁₆ and R₁₇, which may be the same or different, mayeach represent alkyl substituted by one or more of halogen, alkoxyoptionally substituted aryl or optionally substituted aryl, optionallysubstituted aryloxy, aryl or NR₁₀R₁₁, and when R₁₆ or R₁₇ representsNR₁₀R₁₁, one of R₁₀ and R₁₁, may additionally represent CO alkyloptionally substituted or COaryl optionally substituted, and in additionto the definitions shared with R₁₇, R₁₆ may represent hydroxy.
 4. Useaccording to claim 2, in which R₁ and R₂, which may be the same ordifferent, may represent include: alkyl optionally substituted by one ormore halogen, alkoxy or optionally substituted aryl, thioaryl oraryloxy, alkoxy optionally substituted by optionally by alkyl oroptionally substituted aryl, hydroxyl, OC(═W)NR₁₀R₁₁ aryl, thioalkyloptionally substituted by alkyl or optionally substituted aryl,thioaryl, in which the aryl is optionally substituted, NO₂, CN, NR₁₀R₁₁,halogen, SO₂R₁₂, NR₁₃SO₂R₁₄, C(═W)R₁₆, NR₁₅C(═W)R₁₇, P(═O)OR₄₀R₄₁, R₁₀,R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆, R₁₇, R₄₀ and R₄₁, which may be the same ordifferent, represent hydrogen, alkyl optionally substituted byoptionally substituted aryl, optionally substituted aryl, in addition,NR₁₀R₁₁ together with the nitrogen to which they are attached may form aring, R₁₂ may have the same meaning as NR₁₀R₁₁, when R₁₇ representsNR₁₀R₁₁, that NR₁₀R₁₁ may represent hydrogen, COalkyl and CO optionallysubstituted aryl, R₁₆ may represent hydroxy, alkoxy, or NR₁₀R₁₁, R₁₇ mayrepresent alkyl substituted by one or more of halogen, alkoxy,optionally substituted aryl or NR₁₀R₁₁, and when R₁₇ represents NR₁₀R₁₁,that NR₁₀R₁₁ may represent hydrogen, COalkyl and CO optionallysubstituted aryl.
 5. Use of a compound according to claim 1, in which Lrepresents a linker group which is: O, S, (CO)_(n)NR₁₈, n represents aninteger form 0 to 2 alkylene, alkenylene, alkynylene, each of which maybe optionally interrupted by one or more of O, S, NR₁₈, or one or moreC—C single, double or triple bonds, a —N—N— single or double bond, R₁₈represents hydrogen, alkyl, COR₁₆.
 6. Use of a compound according toclaim 1, in which R₄, R₅, R₆, R₇ and R₈, represent hydrogen, alkyl oroptionally substituted aryl.
 7. Use of a compound according to claim 1,in which Y represents N and X represents O, S or NR₄.
 8. Use of compoundaccording to claim 1, in which R₉ represents -L-R₃.
 8. Use of a compoundaccording to claim 1 in which when any of the substituents representsalkyl, alkyl is saturated and has from 1 to 10 carbon atoms.
 10. Use ofa compound according to claim 1, in which aryl is an aromatichydrocarbon or a 5 to 10 membered aromatic heterocyle containing 1 to 4hetero atoms selected from an oxygen atom, a sulphur atom and a nitrogenatom as a ring constituent besides carbon.
 11. Use of a compoundaccording to claim 1, in which aryl is phenyl or naphthalene.
 12. Use ifa compound according to claim 1, in which aryl is furan, thiophene,pyrrole or pyridine.
 13. Use of a compound according to claim 1, inwhich ring B or ring C is a saturated or unsaturated 3 to 10 memberedcarbocylic or heterocyclic ring.
 14. Use of a compound according toclaim 1, in which ring B is benzene ring.
 15. Use of a compoundaccording to claim 1, in which ring C is a 3-10 membered saturated orunsaturated carbocylic ring.
 16. Use of a compound according to claim 1,in which at least one R₁ represents NR₁₅C(═W)R₁₇.
 17. Use of a compoundaccording to claim 1, in which at least one R₁ representsNR_(15c)(═O)R₁₇.
 18. Use of a compound according to claim 1, in which atleast one R₁ represents CONR₁₀R₁₁.
 19. Use of a compound according toclaim 1, in which at least one R₁ represents NHCOR₁₇, wherein R₁₇ isselected from: alkyl C₁-C₆, alkyl C₁-C₆ substituted by phenyl, alkylC₁-C₆ substituted by alkoxy C₁-C₆, haloalkyl C₁-C₆, perfluoroalkylC₁-C₆, phenyl optionally substituted by one or more of halogen, alkylC₁-C₆, alkoxy C₁-C₆, amino, (alkyl C₁-C₆)amino, di(alkyl C₁-C₆) amino orphenyl, CH:CH phenyl, naphthyl, pyridinyl, thiophenyl and furanyl. 20.Use of a compound according to claim 1 in which one or both of R₁ and R₂is other than —COOH.
 21. Use of a compound according to claim 1, inwhich at least one of R₁ represents NR₁₅CONR₁₀R₁₁, wherein R₁₀ and R₁₁,which may be the same or different, are selected from optionallysubstituted aryl, alkyl and COaryl optionally substituted.
 22. Use of acompound according to claim 1, in which at least one of R₁ representsNHCONHR₁₅ and R₁₅ is selected from phenyl, alkyl C₁ to C₆ and COphenyloptionally substituted by one or more halogen.
 23. Use of a compoundaccording to claim 1, in which at least one of R₁ represents alkyl C₁ toC₆, optionally substituted by phenyl or a 4 to 7-membered, preferably 5or 6-membered saturated or unsaturated heterocycle preferably containingone to two heteroatoms selected from N, S and O.
 24. Use of a compoundaccording to claim 1 in which at least one of R₁ represents COR₁₆ andR₁₆ is alkoxy C₁-C₆, amino, (alkyl C₁-C₆)amino or di(alkyl C₁-C₆) amino.25. Use of a compound according to claim 1, in which at least one of R₁represents: NO₂, halogen, amino or (alkyl C₁-C₆)amino or di(alkyl C₁-C₆)amino in which the alkyl C₁ to C₆ is optionally substituted by phenyl ora 5 or 6 membered saturated or unsaturated heterocycle, NHSO₂alkylC₁-C₆, NHSO₂phenyl, SO₂alkyl C₁-C₆, phenyl optionally substituted by C₁to C₆ alkoxy C₁-C₆, a 5-10 membered, saturated or unsaturated, mono- orbi-cyclic heterocycle containing from 1-3 heteroatoms selected from N, Sand O.
 26. Use of a compound according to claim 1, in which R₃ representaryl and is optionally substituted by one to three substituents, R₂,which may be the same or different.
 27. Use of a compound according toclaim 25 in which R₃ is a 5-10 membered aromatic mono- or bi-cyclicsystem.
 28. Use of a compound according to claim 26, in which thearomatic system is a hydrocarbon.
 29. Use of a compound according toclaim 27, in which the aromatic hydrocarbon is benzene or naphthalene.30. Use of a compound according to claim 26, in which the aromaticsystem is a heterocyclic system containing up to three heteroatomsselected from N, O and S.
 31. Use of a compound according to claim 30,in which the heterocyclic system is thiophene, furan, pyridine orpyrrole.
 32. Use of a compound according to claim 2, in which thesubstituent(s) R² is/are selected from is: alkyl C₁-C₆, optionallysubstituted by thiophenyl or phenoxy, each optionally substituted byhalogen, alkoxy C₁-C₆, phenyl, thioalkyl C₁-C₆, thiophenyl, optionallysubstituted by halogen, NO₂, CN NR₁₀R₁₁, in which R₁₀ and R₁₁, which maybe the same or different represent hydrogen, alkyl C₁-C₆, or togetherwith the nitrogen to which they are attached form a 5 to 7 membered ringwhich may contain one or more additional heteroatoms selected from N, Oand S, halogen, SO₂R₁₂, in which R₁₂ represents a 5 to 7 membered ringwhich may contain one or more additional heteroatoms selected from N, Oand S, NHCOR₁₇, in which R₁₇ represents alkyl C₁-C₆, optionallysubstituted by: phenyl or halogen, or phenyl optionally substituted byalkoxy C₁-C₆, carboxy, or halogen, or a 5 or 6 membered saturated orunsaturated heterocycle, phenyl or a 5 or 6 membered saturated orunsaturated heterocycle optionally substituted by halogen, alkoxy C₁ toC₆, carboxy or a group SO₂NR₁₀R₁₁,
 33. Use of a compound according toclaim 32 in which NR₁₀R₁₁ represents N-pyrrole, N-piperidine, N′(C₁-C₆)alkyl N piperazine or N-morpholine.
 34. Use of a compound according toclaim 5 in which the L represents: —NH.NH—, —CH═CH, —NCOR₁₆ in which R₁₆represents phenyl or a 5 or 6 membered saturated or unsaturatedheterocycle optionally substituted by halogen, alkoxy C1 to C6, carboxy.35. Use of a compound according to claim 1 in which two of A₁-A₄represent nitrogen.
 36. Use of a compound according to claim 1 in whichone of A₁-A₄ represents nitrogen.
 37. Use of a compound according toclaim 1 in which all of A₁-A₄ represents CR₁.
 38. Use of a compound aslisted in table 1 according to claim 1.